TY  - JOUR
AU  - Drakulić, Branko
AU  - Stanojković, Tatjana
AU  - Žižak, Željko
AU  - Dabović, Milan
PY  - 2011
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2695
AB  - Antiproliferative activity of 27 phenyl-substituted 4-aryl-4-oxo-2-butenoic acids (aroylacrylic acids) toward Human cervix carcinoma (HeLa), Human chronic myelogenous leukemia (K562) and Human colon tumor (LS174) cell lines in vitro are reported. Compounds are active toward all examined cell lines. The most active compounds bear two or three branched alkyl or cycloalkyl substituents on phenyl moiety having potencies in low micromolar ranges. One of most potent derivatives arrests the cell cycle at S phase in HeLa cells. The 3D QSAR study, using molecular interaction fields (MIF) and derived alignment independent descriptors (GRIND-2), rationalize the structural characteristics correlated with potency of compounds. Covalent chemistry, most possibly involved in the mode of action of reported compounds, was quantitatively accounted using frontier molecular orbitals. Pharmacophoric pattern of most potent compounds are used as a template for virtual screening, to find similar ones in database of compounds screened against DTP-NCI 60 tumor cell lines. Potency of obtained hits is well predicted. © 2011 Elsevier Masson SAS. All rights reserved.
PB  - Elsevier
T2  - European Journal of Medicinal Chemistry
T1  - Antiproliferative activity of aroylacrylic acids. Structure-activity study based on molecular interaction fields
VL  - 46
IS  - 8
SP  - 3265
EP  - 3273
DO  - 10.1016/j.ejmech.2011.04.043
ER  - 

@article{
author = "Drakulić, Branko and Stanojković, Tatjana and Žižak, Željko and Dabović, Milan",
year = "2011",
abstract = "Antiproliferative activity of 27 phenyl-substituted 4-aryl-4-oxo-2-butenoic acids (aroylacrylic acids) toward Human cervix carcinoma (HeLa), Human chronic myelogenous leukemia (K562) and Human colon tumor (LS174) cell lines in vitro are reported. Compounds are active toward all examined cell lines. The most active compounds bear two or three branched alkyl or cycloalkyl substituents on phenyl moiety having potencies in low micromolar ranges. One of most potent derivatives arrests the cell cycle at S phase in HeLa cells. The 3D QSAR study, using molecular interaction fields (MIF) and derived alignment independent descriptors (GRIND-2), rationalize the structural characteristics correlated with potency of compounds. Covalent chemistry, most possibly involved in the mode of action of reported compounds, was quantitatively accounted using frontier molecular orbitals. Pharmacophoric pattern of most potent compounds are used as a template for virtual screening, to find similar ones in database of compounds screened against DTP-NCI 60 tumor cell lines. Potency of obtained hits is well predicted. © 2011 Elsevier Masson SAS. All rights reserved.",
publisher = "Elsevier",
journal = "European Journal of Medicinal Chemistry",
title = "Antiproliferative activity of aroylacrylic acids. Structure-activity study based on molecular interaction fields",
volume = "46",
number = "8",
pages = "3265-3273",
doi = "10.1016/j.ejmech.2011.04.043"
}

Drakulić, B., Stanojković, T., Žižak, Ž.,& Dabović, M.. (2011). Antiproliferative activity of aroylacrylic acids. Structure-activity study based on molecular interaction fields. in European Journal of Medicinal Chemistry
Elsevier., 46(8), 3265-3273.
https://doi.org/10.1016/j.ejmech.2011.04.043

Drakulić B, Stanojković T, Žižak Ž, Dabović M. Antiproliferative activity of aroylacrylic acids. Structure-activity study based on molecular interaction fields. in European Journal of Medicinal Chemistry. 2011;46(8):3265-3273.
doi:10.1016/j.ejmech.2011.04.043 .

Drakulić, Branko, Stanojković, Tatjana, Žižak, Željko, Dabović, Milan, "Antiproliferative activity of aroylacrylic acids. Structure-activity study based on molecular interaction fields" in European Journal of Medicinal Chemistry, 46, no. 8 (2011):3265-3273,
https://doi.org/10.1016/j.ejmech.2011.04.043 . .

TY  - JOUR
AU  - Krstić, Natalija
AU  - Bjelaković, Mira
AU  - Dabović, Milan
AU  - Pavlović, Vladimir D.
PY  - 2010
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/629
AB  - The reactions of selected alpha,beta-unsaturated steroidal ketones with Lawesson's reagent (LR) in CH(2)Cl(2) and toluene under the standard reaction conditions and with a combination of phosphorus pentasulfide with hexamethyldisiloxane (P(4)S(10)/HMDO) in 1,2-dichlorobenzene (ODCB) under microwave irradiation were investigated and for this purpose several cholestane, androstane and pregnane carbonyl derivatives were chosen. Depending on the reagent and the solvent, 19 new sulfur containing compounds, including dithiones 4c and 4d, alpha,beta-unsaturated 3-thiones 3a-e, dimer-sulfides 2a-e, 1,2,4-trithiolanes 5a-e and phosphonotrithioates 6b-e were synthesized. All newly prepared compounds were characterized by IR, (1)H- and (13)C-NMR spectroscopy and elemental analysis.
PB  - MDPI
T2  - Molecules
T1  - Thionation of Some alpha,beta-Unsaturated Steroidal Ketones
VL  - 15
IS  - 5
SP  - 3462
EP  - 3477
DO  - 10.3390/molecules15053462
ER  - 

@article{
author = "Krstić, Natalija and Bjelaković, Mira and Dabović, Milan and Pavlović, Vladimir D.",
year = "2010",
abstract = "The reactions of selected alpha,beta-unsaturated steroidal ketones with Lawesson's reagent (LR) in CH(2)Cl(2) and toluene under the standard reaction conditions and with a combination of phosphorus pentasulfide with hexamethyldisiloxane (P(4)S(10)/HMDO) in 1,2-dichlorobenzene (ODCB) under microwave irradiation were investigated and for this purpose several cholestane, androstane and pregnane carbonyl derivatives were chosen. Depending on the reagent and the solvent, 19 new sulfur containing compounds, including dithiones 4c and 4d, alpha,beta-unsaturated 3-thiones 3a-e, dimer-sulfides 2a-e, 1,2,4-trithiolanes 5a-e and phosphonotrithioates 6b-e were synthesized. All newly prepared compounds were characterized by IR, (1)H- and (13)C-NMR spectroscopy and elemental analysis.",
publisher = "MDPI",
journal = "Molecules",
title = "Thionation of Some alpha,beta-Unsaturated Steroidal Ketones",
volume = "15",
number = "5",
pages = "3462-3477",
doi = "10.3390/molecules15053462"
}

Krstić, N., Bjelaković, M., Dabović, M.,& Pavlović, V. D.. (2010). Thionation of Some alpha,beta-Unsaturated Steroidal Ketones. in Molecules
MDPI., 15(5), 3462-3477.
https://doi.org/10.3390/molecules15053462

Krstić N, Bjelaković M, Dabović M, Pavlović VD. Thionation of Some alpha,beta-Unsaturated Steroidal Ketones. in Molecules. 2010;15(5):3462-3477.
doi:10.3390/molecules15053462 .

Krstić, Natalija, Bjelaković, Mira, Dabović, Milan, Pavlović, Vladimir D., "Thionation of Some alpha,beta-Unsaturated Steroidal Ketones" in Molecules, 15, no. 5 (2010):3462-3477,
https://doi.org/10.3390/molecules15053462 . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Krstić, Natalija
AU  - Todorović, Nina
AU  - Krunić, Aleksej
AU  - Tinant, Bernard
AU  - Dabović, Milan
AU  - Pavlović, Vladimir D.
PY  - 2009
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/620
AB  - In this paper a synthetic pathway to the modified 5,10:13,14-bisfragmentation cholestane derivatives 8-14 is described. The synthesis involves introduction of the 5α- and 14α-hydroxyl groups in the cholestane molecule and subsequent cleavage of the C(5)-C(10) bond in 5α,14α-dihydroxycholestan-3β-yl acetate (4) with the HgO/I2 reagent and the C(13)-C(14) bond in the stereoisomeric 14α-hydroxy-5,10-secosteroids 5 and 6 with the Pb(OAc)4/I2 reagent. Complete and unambiguous 1H and 13C NMR resonance assignments of the obtained secosteroids, as well as the solution conformations of their 10- and 9-membered rings were determined by extensive analysis of 1D and 2D NMR spectral data. The structures and the solid-state conformations of 5,10-secosteroids 5-7 were confirmed by X-ray analysis. All diseco-compounds have a novel 5,10:13,14-disecocholestane skeleton.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - 5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings
VL  - 65
IS  - 46
SP  - 9557
EP  - 9568
DO  - 10.1016/j.tet.2009.09.066
ER  - 

@article{
author = "Bjelaković, Mira and Krstić, Natalija and Todorović, Nina and Krunić, Aleksej and Tinant, Bernard and Dabović, Milan and Pavlović, Vladimir D.",
year = "2009",
abstract = "In this paper a synthetic pathway to the modified 5,10:13,14-bisfragmentation cholestane derivatives 8-14 is described. The synthesis involves introduction of the 5α- and 14α-hydroxyl groups in the cholestane molecule and subsequent cleavage of the C(5)-C(10) bond in 5α,14α-dihydroxycholestan-3β-yl acetate (4) with the HgO/I2 reagent and the C(13)-C(14) bond in the stereoisomeric 14α-hydroxy-5,10-secosteroids 5 and 6 with the Pb(OAc)4/I2 reagent. Complete and unambiguous 1H and 13C NMR resonance assignments of the obtained secosteroids, as well as the solution conformations of their 10- and 9-membered rings were determined by extensive analysis of 1D and 2D NMR spectral data. The structures and the solid-state conformations of 5,10-secosteroids 5-7 were confirmed by X-ray analysis. All diseco-compounds have a novel 5,10:13,14-disecocholestane skeleton.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings",
volume = "65",
number = "46",
pages = "9557-9568",
doi = "10.1016/j.tet.2009.09.066"
}

Bjelaković, M., Krstić, N., Todorović, N., Krunić, A., Tinant, B., Dabović, M.,& Pavlović, V. D.. (2009). 5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 65(46), 9557-9568.
https://doi.org/10.1016/j.tet.2009.09.066

Bjelaković M, Krstić N, Todorović N, Krunić A, Tinant B, Dabović M, Pavlović VD. 5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings. in Tetrahedron. 2009;65(46):9557-9568.
doi:10.1016/j.tet.2009.09.066 .

Bjelaković, Mira, Krstić, Natalija, Todorović, Nina, Krunić, Aleksej, Tinant, Bernard, Dabović, Milan, Pavlović, Vladimir D., "5,10:13,14-Disecosteroids: novel modified steroids containing 10- and 9-membered rings" in Tetrahedron, 65, no. 46 (2009):9557-9568,
https://doi.org/10.1016/j.tet.2009.09.066 . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Krstić, Natalija
AU  - Juranić, Nenad
AU  - Dabović, Milan
AU  - Gojković, S.V.
AU  - Kessler, M.
AU  - Kalvoda, J.
AU  - Pavlović, Vladimir D.
PY  - 2007
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/358
AB  - We report herein the synthesis of a novel modified steroid with two rigidly positioned amino acids in C- and N-protected forms (Gly-OtBu and N-Fmoc-l-Phe) at the angular positions (C-18 methylamino group and C-19 carboxylic function) of the steroid nucleus via amide bonds, starting from 18-cyanopregnenolone acetate over 10 steps. In an attempt to gain more insight into the structural and conformational features of this novel 18-Phe,19-Gly-containing steroidal compound, we describe the detailed 2D NMR spectral analysis. Despite the large size and the conformational flexibility of the amino acid units in this molecule, conformational analysis by NOESY connectivities showed the existence of mainly one conformation (∼95%) in CDCl3 solution with approximately parallel orientation of the phenylalanine and glycine moieties.
PB  - Oxford : Pergamon-Elsevier Science Ltd
T2  - Tetrahedron
T1  - Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound
VL  - 63
IS  - 40
SP  - 9960
EP  - 9969
DO  - 10.1016/j.tet.2007.07.056
ER  - 

@article{
author = "Bjelaković, Mira and Krstić, Natalija and Juranić, Nenad and Dabović, Milan and Gojković, S.V. and Kessler, M. and Kalvoda, J. and Pavlović, Vladimir D.",
year = "2007",
abstract = "We report herein the synthesis of a novel modified steroid with two rigidly positioned amino acids in C- and N-protected forms (Gly-OtBu and N-Fmoc-l-Phe) at the angular positions (C-18 methylamino group and C-19 carboxylic function) of the steroid nucleus via amide bonds, starting from 18-cyanopregnenolone acetate over 10 steps. In an attempt to gain more insight into the structural and conformational features of this novel 18-Phe,19-Gly-containing steroidal compound, we describe the detailed 2D NMR spectral analysis. Despite the large size and the conformational flexibility of the amino acid units in this molecule, conformational analysis by NOESY connectivities showed the existence of mainly one conformation (∼95%) in CDCl3 solution with approximately parallel orientation of the phenylalanine and glycine moieties.",
publisher = "Oxford : Pergamon-Elsevier Science Ltd",
journal = "Tetrahedron",
title = "Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound",
volume = "63",
number = "40",
pages = "9960-9969",
doi = "10.1016/j.tet.2007.07.056"
}

Bjelaković, M., Krstić, N., Juranić, N., Dabović, M., Gojković, S.V., Kessler, M., Kalvoda, J.,& Pavlović, V. D.. (2007). Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound. in Tetrahedron
Oxford : Pergamon-Elsevier Science Ltd., 63(40), 9960-9969.
https://doi.org/10.1016/j.tet.2007.07.056

Bjelaković M, Krstić N, Juranić N, Dabović M, Gojković S, Kessler M, Kalvoda J, Pavlović VD. Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound. in Tetrahedron. 2007;63(40):9960-9969.
doi:10.1016/j.tet.2007.07.056 .

Bjelaković, Mira, Krstić, Natalija, Juranić, Nenad, Dabović, Milan, Gojković, S.V., Kessler, M., Kalvoda, J., Pavlović, Vladimir D., "Steroid template associated peptides: design, synthesis and 2D NMR characterization of a novel protected 18-Phe,19-Gly-containing steroidal compound" in Tetrahedron, 63, no. 40 (2007):9960-9969,
https://doi.org/10.1016/j.tet.2007.07.056 . .

TY  - JOUR
AU  - Pavlović, Vladimir D.
AU  - Dabović, Milan
AU  - Martinović, Saša B.
AU  - Lorenc, Ljubinka
AU  - Kalvoda, J
PY  - 2004
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2705
AB  - In the present paper, the preparation of 3β-hydroxy-17β-dimethyl- tert-butylsilyloxy-5-azaandrostane (15) in fourteen steps is described. B-nor-17-oxoandrost-5-en-3β-yl acetate (1) 1,2 was used as the starting material, which was transformed to the key intermediate of the synthesis, B-nor-17β-dimethyl-tert-butylsilyloxyandrost-4-en-3β-yl acetate (7).
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis of 5-azaandrostane-3β,17β-diol protected at the 17β-hydroxyl group
VL  - 69
IS  - 11
SP  - 861
EP  - 869
DO  - 10.2298/JSC0411861P
ER  - 

@article{
author = "Pavlović, Vladimir D. and Dabović, Milan and Martinović, Saša B. and Lorenc, Ljubinka and Kalvoda, J",
year = "2004",
abstract = "In the present paper, the preparation of 3β-hydroxy-17β-dimethyl- tert-butylsilyloxy-5-azaandrostane (15) in fourteen steps is described. B-nor-17-oxoandrost-5-en-3β-yl acetate (1) 1,2 was used as the starting material, which was transformed to the key intermediate of the synthesis, B-nor-17β-dimethyl-tert-butylsilyloxyandrost-4-en-3β-yl acetate (7).",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis of 5-azaandrostane-3β,17β-diol protected at the 17β-hydroxyl group",
volume = "69",
number = "11",
pages = "861-869",
doi = "10.2298/JSC0411861P"
}

Pavlović, V. D., Dabović, M., Martinović, S. B., Lorenc, L.,& Kalvoda, J.. (2004). Synthesis of 5-azaandrostane-3β,17β-diol protected at the 17β-hydroxyl group. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 69(11), 861-869.
https://doi.org/10.2298/JSC0411861P

Pavlović VD, Dabović M, Martinović SB, Lorenc L, Kalvoda J. Synthesis of 5-azaandrostane-3β,17β-diol protected at the 17β-hydroxyl group. in Journal of the Serbian Chemical Society. 2004;69(11):861-869.
doi:10.2298/JSC0411861P .

Pavlović, Vladimir D., Dabović, Milan, Martinović, Saša B., Lorenc, Ljubinka, Kalvoda, J, "Synthesis of 5-azaandrostane-3β,17β-diol protected at the 17β-hydroxyl group" in Journal of the Serbian Chemical Society, 69, no. 11 (2004):861-869,
https://doi.org/10.2298/JSC0411861P . .

TY  - JOUR
AU  - Krstić, Natalija
AU  - Bjelaković, Mira
AU  - Dabović, Milan
AU  - Lorenc, Ljubinka
AU  - Pavlović, Vladimir D.
PY  - 2004
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/148
AB  - Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime (4) (prepared in 4 steps starting from cholest-5-en-3β-ol ο1)) with thionyl chloride in dioxane solution afforded an enamide-type lactam, i.e. 7-aza-B-homocholest-4-en-6-one (6) as a single product. Photoreaction of the same compound in methanol or benzene-acetic acid solution gave a mixture of products, with the formation of the parent ketone 3 and the occurrence of Z/E isomerization, while the lactam 6 was obtained only when the reaction was performed in methanol and then in very low yield (7%).
AB  - Bekmanovo premeštanje (Z)-holest-4-en-6-on oksima (4) (koji je dobijen u 4 faze, polazeći od holest-5-en-3 β-ola (1)) sa tionil-hloridom u dioksanskom rastvoru, kao jedini proizvod daje laktam enamidnog tipa, tj. 7-aza-B-homoholest-4-en-6-on (6). Fotoreakcijom istog jedinjenja u metanolu ili u rastvoru benzen-sirćetna kiselina, nastaje smesa proizvoda koju čine polazni keton 3 i proizvodi Z/E izomerizacije, dok je laktam 6 dobiven u vrlo niskom prinosu (7%) samo u metanolnom rastvoru.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime
T1  - Fotohemijsko i Bekmanovo premeštanje(z)-holest-4-en-6-on oksima
VL  - 69
IS  - 6
SP  - 413
EP  - 420
DO  - 10.2298/JSC0406413K
ER  - 

@article{
author = "Krstić, Natalija and Bjelaković, Mira and Dabović, Milan and Lorenc, Ljubinka and Pavlović, Vladimir D.",
year = "2004",
abstract = "Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime (4) (prepared in 4 steps starting from cholest-5-en-3β-ol ο1)) with thionyl chloride in dioxane solution afforded an enamide-type lactam, i.e. 7-aza-B-homocholest-4-en-6-one (6) as a single product. Photoreaction of the same compound in methanol or benzene-acetic acid solution gave a mixture of products, with the formation of the parent ketone 3 and the occurrence of Z/E isomerization, while the lactam 6 was obtained only when the reaction was performed in methanol and then in very low yield (7%)., Bekmanovo premeštanje (Z)-holest-4-en-6-on oksima (4) (koji je dobijen u 4 faze, polazeći od holest-5-en-3 β-ola (1)) sa tionil-hloridom u dioksanskom rastvoru, kao jedini proizvod daje laktam enamidnog tipa, tj. 7-aza-B-homoholest-4-en-6-on (6). Fotoreakcijom istog jedinjenja u metanolu ili u rastvoru benzen-sirćetna kiselina, nastaje smesa proizvoda koju čine polazni keton 3 i proizvodi Z/E izomerizacije, dok je laktam 6 dobiven u vrlo niskom prinosu (7%) samo u metanolnom rastvoru.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime, Fotohemijsko i Bekmanovo premeštanje(z)-holest-4-en-6-on oksima",
volume = "69",
number = "6",
pages = "413-420",
doi = "10.2298/JSC0406413K"
}

Krstić, N., Bjelaković, M., Dabović, M., Lorenc, L.,& Pavlović, V. D.. (2004). Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 69(6), 413-420.
https://doi.org/10.2298/JSC0406413K

Krstić N, Bjelaković M, Dabović M, Lorenc L, Pavlović VD. Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime. in Journal of the Serbian Chemical Society. 2004;69(6):413-420.
doi:10.2298/JSC0406413K .

Krstić, Natalija, Bjelaković, Mira, Dabović, Milan, Lorenc, Ljubinka, Pavlović, Vladimir D., "Photochemical and Beckmann rearrangement of (Z)-cholest-4-en-6-one oxime" in Journal of the Serbian Chemical Society, 69, no. 6 (2004):413-420,
https://doi.org/10.2298/JSC0406413K . .

TY  - JOUR
AU  - Bjelaković, Mira
AU  - Pavlović, Vladimir D.
AU  - Dabović, Milan
AU  - Lorenc, Ljubinka
PY  - 2003
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/115
AB  - The acid-catalyzed reaction of (Z)- and (E)-B-nor-5,10-seco-ketones 2 and 3 resulted in an intramolecular cyclization to give the 5-hydroxy-A-nor-1β,5β-10(19)-methylidene derivative 8, the 5β-hydroxy-A-nor-1(10)-unsaturated compound 9 and the 5β,10β-dihydroxy A-nor-product 10, from the (Z)-isomer and the 5-hydroxy-A-nor-1β,5β-10(19)-methylidene product 11, from the (E)-isomer. Upon UV-irradiation, the (Z)- and (E)-seco-ketones 2 and 3 underwent a reversible (Z)/(E) and (E)/(Z)-isomerization and in addition to a transannular photocyclization to afford the 10(19)-methylidene derivatives 8 and 11, respectively, while photolysis of the 10(19)-methylidene-B-nor-5,10-seco-ketone 4 gave the oxetane derivative 12.
AB  - Kiselo-katalizovana reakcija (Z)- i (E)-B-nor-5,10-seko-ketona 2 i 3 rezultuje u intramolekulskoj ciklizaciji dajući 5-hidroksi-A-nor-1β,5β-10(19)-metilidenski derivat 8, 5β-hidroksi A-nor-1(10)-nezasićeno jedinjenje 9 i 5β,10β-dihidroksi-A-nor-proizvod 10, iz Z-izomera, i 5-hidroksi-A-nor-1β,5β-10(19)-metilidenski proizvod 11, iz E-izomera. (Z)- i (E)-Seko- ketoni 2 i 3 UV-ozračivanjem podležu reverzibilnoj (Z)/(E) odnosno (E)/(Z) izomerizaciji, kao i transanularnoj fotociklizaciji dajući 10(19)-metilidenske derivate 8 odnosno 11, dok se fotolizom 10(19)-metilidenskog-5,10-seko-ketona 4 gradi oksetanski derivat 12.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Acid-catalyzed and photolytic reactivity of some unsaturated B-nor-5, 10-secosteroidal ketones
T1  - Kiselo-katalizovana i fotolitička reaktivnost nekih nezasićenih B-nor-5,10-sekosteroidnih ketona
VL  - 68
IS  - 4-5
SP  - 303
EP  - 312
DO  - 10.2298/JSC0305303B
ER  - 

@article{
author = "Bjelaković, Mira and Pavlović, Vladimir D. and Dabović, Milan and Lorenc, Ljubinka",
year = "2003",
abstract = "The acid-catalyzed reaction of (Z)- and (E)-B-nor-5,10-seco-ketones 2 and 3 resulted in an intramolecular cyclization to give the 5-hydroxy-A-nor-1β,5β-10(19)-methylidene derivative 8, the 5β-hydroxy-A-nor-1(10)-unsaturated compound 9 and the 5β,10β-dihydroxy A-nor-product 10, from the (Z)-isomer and the 5-hydroxy-A-nor-1β,5β-10(19)-methylidene product 11, from the (E)-isomer. Upon UV-irradiation, the (Z)- and (E)-seco-ketones 2 and 3 underwent a reversible (Z)/(E) and (E)/(Z)-isomerization and in addition to a transannular photocyclization to afford the 10(19)-methylidene derivatives 8 and 11, respectively, while photolysis of the 10(19)-methylidene-B-nor-5,10-seco-ketone 4 gave the oxetane derivative 12., Kiselo-katalizovana reakcija (Z)- i (E)-B-nor-5,10-seko-ketona 2 i 3 rezultuje u intramolekulskoj ciklizaciji dajući 5-hidroksi-A-nor-1β,5β-10(19)-metilidenski derivat 8, 5β-hidroksi A-nor-1(10)-nezasićeno jedinjenje 9 i 5β,10β-dihidroksi-A-nor-proizvod 10, iz Z-izomera, i 5-hidroksi-A-nor-1β,5β-10(19)-metilidenski proizvod 11, iz E-izomera. (Z)- i (E)-Seko- ketoni 2 i 3 UV-ozračivanjem podležu reverzibilnoj (Z)/(E) odnosno (E)/(Z) izomerizaciji, kao i transanularnoj fotociklizaciji dajući 10(19)-metilidenske derivate 8 odnosno 11, dok se fotolizom 10(19)-metilidenskog-5,10-seko-ketona 4 gradi oksetanski derivat 12.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Acid-catalyzed and photolytic reactivity of some unsaturated B-nor-5, 10-secosteroidal ketones, Kiselo-katalizovana i fotolitička reaktivnost nekih nezasićenih B-nor-5,10-sekosteroidnih ketona",
volume = "68",
number = "4-5",
pages = "303-312",
doi = "10.2298/JSC0305303B"
}

Bjelaković, M., Pavlović, V. D., Dabović, M.,& Lorenc, L.. (2003). Acid-catalyzed and photolytic reactivity of some unsaturated B-nor-5, 10-secosteroidal ketones. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 68(4-5), 303-312.
https://doi.org/10.2298/JSC0305303B

Bjelaković M, Pavlović VD, Dabović M, Lorenc L. Acid-catalyzed and photolytic reactivity of some unsaturated B-nor-5, 10-secosteroidal ketones. in Journal of the Serbian Chemical Society. 2003;68(4-5):303-312.
doi:10.2298/JSC0305303B .

Bjelaković, Mira, Pavlović, Vladimir D., Dabović, Milan, Lorenc, Ljubinka, "Acid-catalyzed and photolytic reactivity of some unsaturated B-nor-5, 10-secosteroidal ketones" in Journal of the Serbian Chemical Society, 68, no. 4-5 (2003):303-312,
https://doi.org/10.2298/JSC0305303B . .

TY  - JOUR
AU  - Dabović, Milan
AU  - Petrović, Ivanka J.
AU  - Krstić, Natalija
AU  - Lorenc, Ljubinka
PY  - 2000
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/11
AB  - Expoxidation of cholesta-5,8-dien-3β-yl acetate (1) with peracids takes place preferentially at the more highly substituted Δ8-olefinic double bond to give: (a) with monoperphthalic acid, 8α,9α-epoxycholest-5-en-3β-yl acetate (2) (in 39 % yield) and 9α-hydroxy-5α,6α-epoxycholest-8(14)-en-3β-yl acetate (3) (in 30 % yield); and (b) with m-chloroperbenzoic acid, the 8α,9α-epoxide 2 (64 %) and 5α,6α-epoxy derivative 3 (20 %). Some chemical transformations of the obtained epoxides are described.
AB  - Epoksidacija holesta-5,8-dien-3β-il acetata (1) sa perkiselinama prvenstveno se odvija na više supstituisanoj Δ8-olefinskoj dvoguboj vezi pri čemu se dobija: (a) sa monoperftalnom kiselinom, 8α,9α-epoksiholest-5-en-3β-il acetat (2) (u prenosu od 39 %) i 9α-hidroksi-5α,6α-epoksiholest-8(14)-en-3β-il acetat (3) (u prenosu od 30 %); i (b) sa m-hlorperbenzoevom kiselinom, 8α,9α-epoksid 2 (u prenosu od 64 %) i 5α,6α-epoksi derivat 3 (u prenosu od 20 %). Opisane su i neke hemijske transformacije dobijenih epoksida.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Peracids oxidation of cholesta-5,8-dien-3β-yl acetate
T1  - Oksidacija holesta-5,8-dien-3β-il acetata sa perkiselinama
VL  - 65
IS  - 11
SP  - 769
EP  - 772
UR  - https://hdl.handle.net/21.15107/rcub_cer_11
ER  - 

@article{
author = "Dabović, Milan and Petrović, Ivanka J. and Krstić, Natalija and Lorenc, Ljubinka",
year = "2000",
abstract = "Expoxidation of cholesta-5,8-dien-3β-yl acetate (1) with peracids takes place preferentially at the more highly substituted Δ8-olefinic double bond to give: (a) with monoperphthalic acid, 8α,9α-epoxycholest-5-en-3β-yl acetate (2) (in 39 % yield) and 9α-hydroxy-5α,6α-epoxycholest-8(14)-en-3β-yl acetate (3) (in 30 % yield); and (b) with m-chloroperbenzoic acid, the 8α,9α-epoxide 2 (64 %) and 5α,6α-epoxy derivative 3 (20 %). Some chemical transformations of the obtained epoxides are described., Epoksidacija holesta-5,8-dien-3β-il acetata (1) sa perkiselinama prvenstveno se odvija na više supstituisanoj Δ8-olefinskoj dvoguboj vezi pri čemu se dobija: (a) sa monoperftalnom kiselinom, 8α,9α-epoksiholest-5-en-3β-il acetat (2) (u prenosu od 39 %) i 9α-hidroksi-5α,6α-epoksiholest-8(14)-en-3β-il acetat (3) (u prenosu od 30 %); i (b) sa m-hlorperbenzoevom kiselinom, 8α,9α-epoksid 2 (u prenosu od 64 %) i 5α,6α-epoksi derivat 3 (u prenosu od 20 %). Opisane su i neke hemijske transformacije dobijenih epoksida.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Peracids oxidation of cholesta-5,8-dien-3β-yl acetate, Oksidacija holesta-5,8-dien-3β-il acetata sa perkiselinama",
volume = "65",
number = "11",
pages = "769-772",
url = "https://hdl.handle.net/21.15107/rcub_cer_11"
}

Dabović, M., Petrović, I. J., Krstić, N.,& Lorenc, L.. (2000). Peracids oxidation of cholesta-5,8-dien-3β-yl acetate. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 65(11), 769-772.
https://hdl.handle.net/21.15107/rcub_cer_11

Dabović M, Petrović IJ, Krstić N, Lorenc L. Peracids oxidation of cholesta-5,8-dien-3β-yl acetate. in Journal of the Serbian Chemical Society. 2000;65(11):769-772.
https://hdl.handle.net/21.15107/rcub_cer_11 .

Dabović, Milan, Petrović, Ivanka J., Krstić, Natalija, Lorenc, Ljubinka, "Peracids oxidation of cholesta-5,8-dien-3β-yl acetate" in Journal of the Serbian Chemical Society, 65, no. 11 (2000):769-772,
https://hdl.handle.net/21.15107/rcub_cer_11 .

TY  - JOUR
AU  - Lorenc, Ljubinka B.
AU  - Pavlović, Vladimir
AU  - Juranić, Ivan
AU  - Mihailović, Milhailo Lj.
AU  - Bondarenko-Gheorghiu, Lidija G.
AU  - Krstić, Natalija
AU  - Dabović, Milan
PY  - 1999
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4401
AB  - The thermal and acid-catalyzed intramolecular rearrangement of the (Z)- and (E)-cyclodecene-1,4-dione compounds deriving from steroids, 2a,b and 3a,b, respectively, proceeds stereoselectively to give the corresponding configurationally different spiro-γ-lactone derivatives, the (5R,9R)-isomers 4a,b (from the (Z)-cyclodecenediones 2a,b) and the (5R,9S)-isomers 5a,b (from the (E)-cyclodecenediones 3a,b). The semiempirical MNDOAM1 and PM3 molecular orbital methods were applied to elucidate the possible mechanistic pathway of the observed intramolecular process leading to the spiro-γ-lactone structures.
PB  - MDPI
T2  - Molecules
T1  - Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study
VL  - 4
IS  - 10
SP  - 272
EP  - 278
DO  - 10.3390/41000272
ER  - 

@article{
author = "Lorenc, Ljubinka B. and Pavlović, Vladimir and Juranić, Ivan and Mihailović, Milhailo Lj. and Bondarenko-Gheorghiu, Lidija G. and Krstić, Natalija and Dabović, Milan",
year = "1999",
abstract = "The thermal and acid-catalyzed intramolecular rearrangement of the (Z)- and (E)-cyclodecene-1,4-dione compounds deriving from steroids, 2a,b and 3a,b, respectively, proceeds stereoselectively to give the corresponding configurationally different spiro-γ-lactone derivatives, the (5R,9R)-isomers 4a,b (from the (Z)-cyclodecenediones 2a,b) and the (5R,9S)-isomers 5a,b (from the (E)-cyclodecenediones 3a,b). The semiempirical MNDOAM1 and PM3 molecular orbital methods were applied to elucidate the possible mechanistic pathway of the observed intramolecular process leading to the spiro-γ-lactone structures.",
publisher = "MDPI",
journal = "Molecules",
title = "Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study",
volume = "4",
number = "10",
pages = "272-278",
doi = "10.3390/41000272"
}

Lorenc, L. B., Pavlović, V., Juranić, I., Mihailović, M. Lj., Bondarenko-Gheorghiu, L. G., Krstić, N.,& Dabović, M.. (1999). Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study. in Molecules
MDPI., 4(10), 272-278.
https://doi.org/10.3390/41000272

Lorenc LB, Pavlović V, Juranić I, Mihailović ML, Bondarenko-Gheorghiu LG, Krstić N, Dabović M. Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study. in Molecules. 1999;4(10):272-278.
doi:10.3390/41000272 .

Lorenc, Ljubinka B., Pavlović, Vladimir, Juranić, Ivan, Mihailović, Milhailo Lj., Bondarenko-Gheorghiu, Lidija G., Krstić, Natalija, Dabović, Milan, "Stereoselective transformation of cyclodecene-1,4-dione systems, derived from steroids, to the corresponding spiro-g-lactones. A semiempirical MO Study" in Molecules, 4, no. 10 (1999):272-278,
https://doi.org/10.3390/41000272 . .

TY  - JOUR
AU  - Stevović, Ljubomir S.
AU  - Pavlović, Vladimir D.
AU  - Martinović, Saša B.
AU  - Dabović, Milan
AU  - Juranić, Ivan
PY  - 1998
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2706
AB  - A simple one-put procedure for the synthesis of the 5,6-seco-steroidal acids 9a,b in described in this paper. It consists of the epoxidation of the ▲ 5 -steroids, i.e., cholesteryl acetate (8a) and 17-oxo-aandrost-5-en-3β-yl acetate (8b) with peracetic acid (generated in situ by the H 2 WO 4 H 2 O 2 system), followed by the CrO 3 /H 2 SO_ oxidation of the thus formed epoxides. The 5,6-seco-steroidal acids 9a,b (obtained in about 90% and 77% yield, respectively) are transformed to the corresponding B-norsteroids by the known method (Beayer-Villiger oxidation and subsequent thermolysis of the respective β-lactones).
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - An improved approach to B-norsteroids: An one-pot preparation of 3β-acetoxy-5-oxo-5,6-seco-cholestan-6-oic and 3β-acetoxy-5,17-dioxo-5,6-seco-androstan-6-oic acids
VL  - 63
IS  - 12
SP  - 955
EP  - 959
UR  - https://hdl.handle.net/21.15107/rcub_cer_2706
ER  - 

@article{
author = "Stevović, Ljubomir S. and Pavlović, Vladimir D. and Martinović, Saša B. and Dabović, Milan and Juranić, Ivan",
year = "1998",
abstract = "A simple one-put procedure for the synthesis of the 5,6-seco-steroidal acids 9a,b in described in this paper. It consists of the epoxidation of the ▲ 5 -steroids, i.e., cholesteryl acetate (8a) and 17-oxo-aandrost-5-en-3β-yl acetate (8b) with peracetic acid (generated in situ by the H 2 WO 4 H 2 O 2 system), followed by the CrO 3 /H 2 SO_ oxidation of the thus formed epoxides. The 5,6-seco-steroidal acids 9a,b (obtained in about 90% and 77% yield, respectively) are transformed to the corresponding B-norsteroids by the known method (Beayer-Villiger oxidation and subsequent thermolysis of the respective β-lactones).",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "An improved approach to B-norsteroids: An one-pot preparation of 3β-acetoxy-5-oxo-5,6-seco-cholestan-6-oic and 3β-acetoxy-5,17-dioxo-5,6-seco-androstan-6-oic acids",
volume = "63",
number = "12",
pages = "955-959",
url = "https://hdl.handle.net/21.15107/rcub_cer_2706"
}

Stevović, L. S., Pavlović, V. D., Martinović, S. B., Dabović, M.,& Juranić, I.. (1998). An improved approach to B-norsteroids: An one-pot preparation of 3β-acetoxy-5-oxo-5,6-seco-cholestan-6-oic and 3β-acetoxy-5,17-dioxo-5,6-seco-androstan-6-oic acids. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 63(12), 955-959.
https://hdl.handle.net/21.15107/rcub_cer_2706

Stevović LS, Pavlović VD, Martinović SB, Dabović M, Juranić I. An improved approach to B-norsteroids: An one-pot preparation of 3β-acetoxy-5-oxo-5,6-seco-cholestan-6-oic and 3β-acetoxy-5,17-dioxo-5,6-seco-androstan-6-oic acids. in Journal of the Serbian Chemical Society. 1998;63(12):955-959.
https://hdl.handle.net/21.15107/rcub_cer_2706 .

Stevović, Ljubomir S., Pavlović, Vladimir D., Martinović, Saša B., Dabović, Milan, Juranić, Ivan, "An improved approach to B-norsteroids: An one-pot preparation of 3β-acetoxy-5-oxo-5,6-seco-cholestan-6-oic and 3β-acetoxy-5,17-dioxo-5,6-seco-androstan-6-oic acids" in Journal of the Serbian Chemical Society, 63, no. 12 (1998):955-959,
https://hdl.handle.net/21.15107/rcub_cer_2706 .

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Dabović, Milan
AU  - Pavlović, Vladimir D.
AU  - Krstić, Natalija
AU  - Lorenc, Ljubinka
PY  - 1997
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2707
AB  - 5-Hydroxy-5α-cholest-8-en-3β-yl acetate (8) (prepared in 6 steps starting from 7-dehydrocholesteryl acetate (1) was transformed with ruthenium tetroxide to 5-hydroxy-8,9-dioxo-8,9-seco-5α-cholestan-3β-yl acetate (9). Treatment of the latter 8,9-seco-5-hydroxy derivative with lead tetraacetate (LTA) or mercuric oxide/iodine reagent (HgO/I2) resulted, instead of the expected oxidative β-fragmentation of its C(5)-C(10) bond, in the competing non-regio and non-stereoselective acetoxylation of the α-positions next to the 8- and 9-oxo functions (with LTA), and in the ≈ 82% recovery of the starting material (with HgO/I2). The results are discussed in terms of the strong hydrogen bonding which exists between the 5α-hydroxyl and the 8-oxo group.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate
VL  - 62
IS  - 9
SP  - 719
EP  - 726
UR  - https://hdl.handle.net/21.15107/rcub_cer_2707
ER  - 

@article{
author = "Mihailović, Milhailo Lj. and Dabović, Milan and Pavlović, Vladimir D. and Krstić, Natalija and Lorenc, Ljubinka",
year = "1997",
abstract = "5-Hydroxy-5α-cholest-8-en-3β-yl acetate (8) (prepared in 6 steps starting from 7-dehydrocholesteryl acetate (1) was transformed with ruthenium tetroxide to 5-hydroxy-8,9-dioxo-8,9-seco-5α-cholestan-3β-yl acetate (9). Treatment of the latter 8,9-seco-5-hydroxy derivative with lead tetraacetate (LTA) or mercuric oxide/iodine reagent (HgO/I2) resulted, instead of the expected oxidative β-fragmentation of its C(5)-C(10) bond, in the competing non-regio and non-stereoselective acetoxylation of the α-positions next to the 8- and 9-oxo functions (with LTA), and in the ≈ 82% recovery of the starting material (with HgO/I2). The results are discussed in terms of the strong hydrogen bonding which exists between the 5α-hydroxyl and the 8-oxo group.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate",
volume = "62",
number = "9",
pages = "719-726",
url = "https://hdl.handle.net/21.15107/rcub_cer_2707"
}

Mihailović, M. Lj., Dabović, M., Pavlović, V. D., Krstić, N.,& Lorenc, L.. (1997). Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 62(9), 719-726.
https://hdl.handle.net/21.15107/rcub_cer_2707

Mihailović ML, Dabović M, Pavlović VD, Krstić N, Lorenc L. Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate. in Journal of the Serbian Chemical Society. 1997;62(9):719-726.
https://hdl.handle.net/21.15107/rcub_cer_2707 .

Mihailović, Milhailo Lj., Dabović, Milan, Pavlović, Vladimir D., Krstić, Natalija, Lorenc, Ljubinka, "Synthesis and oxidative transformations of 5-hydroxy-5α-cholest-8-en-3β-yl acetate" in Journal of the Serbian Chemical Society, 62, no. 9 (1997):719-726,
https://hdl.handle.net/21.15107/rcub_cer_2707 .

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Pavlović, Vladimir D.
AU  - Bondarenko-Gheorghiu, Lidija
AU  - Krstić, Natalija
AU  - Dabović, Milan
AU  - Lorenc, Ljubinka
PY  - 1996
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2708
AB  - In this paper is described a synthetic pathway to the modified 5, 10:8, 14-bisfragmentation cholestene derivatives 10, 11 and 12, which involves introduction of the Δ8(14)-double bond and 5α-hydroxyl group in the cholestane molecule and subsequent cleavage of the olefinic C(8)-C(14) bond (with ruthenium tetroxide) and C(5)-C(10) bond (with mercuric oxide/iodine or lead tetracetate/iodine).
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis of modified 5,10:8,14-bisfragmentation cholestane derivatives
VL  - 61
IS  - 11
SP  - 941
EP  - 946
UR  - https://hdl.handle.net/21.15107/rcub_cer_2708
ER  - 

@article{
author = "Mihailović, Milhailo Lj. and Pavlović, Vladimir D. and Bondarenko-Gheorghiu, Lidija and Krstić, Natalija and Dabović, Milan and Lorenc, Ljubinka",
year = "1996",
abstract = "In this paper is described a synthetic pathway to the modified 5, 10:8, 14-bisfragmentation cholestene derivatives 10, 11 and 12, which involves introduction of the Δ8(14)-double bond and 5α-hydroxyl group in the cholestane molecule and subsequent cleavage of the olefinic C(8)-C(14) bond (with ruthenium tetroxide) and C(5)-C(10) bond (with mercuric oxide/iodine or lead tetracetate/iodine).",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis of modified 5,10:8,14-bisfragmentation cholestane derivatives",
volume = "61",
number = "11",
pages = "941-946",
url = "https://hdl.handle.net/21.15107/rcub_cer_2708"
}

Mihailović, M. Lj., Pavlović, V. D., Bondarenko-Gheorghiu, L., Krstić, N., Dabović, M.,& Lorenc, L.. (1996). Synthesis of modified 5,10:8,14-bisfragmentation cholestane derivatives. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 61(11), 941-946.
https://hdl.handle.net/21.15107/rcub_cer_2708

Mihailović ML, Pavlović VD, Bondarenko-Gheorghiu L, Krstić N, Dabović M, Lorenc L. Synthesis of modified 5,10:8,14-bisfragmentation cholestane derivatives. in Journal of the Serbian Chemical Society. 1996;61(11):941-946.
https://hdl.handle.net/21.15107/rcub_cer_2708 .

Mihailović, Milhailo Lj., Pavlović, Vladimir D., Bondarenko-Gheorghiu, Lidija, Krstić, Natalija, Dabović, Milan, Lorenc, Ljubinka, "Synthesis of modified 5,10:8,14-bisfragmentation cholestane derivatives" in Journal of the Serbian Chemical Society, 61, no. 11 (1996):941-946,
https://hdl.handle.net/21.15107/rcub_cer_2708 .

TY  - JOUR
AU  - Dabović, Milan
AU  - Bjelaković, Mira
AU  - Andrejević, V.
AU  - Lorenc, Ljubinka
AU  - Mihailović, Milhailo Lj.
PY  - 1994
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2697
AB  - Photochemically induced HgO/I2 oxidation of cholest-5-en-3α-ol (6) and cholest-5-en-3β-ol (7) afforded (Scheme 3) products arising from the corresponding alkoxy radicals (12, 13 and 14a,b) and from attack of the I2O intermediate at the olefinic double bond (epoxides 15a and 16a,b respectively). With cholest-5-ene-1α,3β-diol 3-acetate (8) and cholest-7-ene-3β,5α-diol 3-acetate (9) the HgO/I2 oxidation led to unresolvable complex mixtures (Scheme 5). With the same reagent cholest-5-en-3α-ol acetate (10) and cholest-5-en-3β-ol acetate (11) underwent exclusively attack by I2O, to give epoxides 20a,b, iodohydrin 21, and rearranged products 19 and 22 (Scheme 7), in the case of 10, and predominantly epoxides 23a,b (Scheme 8), in the case of 11. © 1994.
PB  - Pergamon
T2  - Tetrahedron
T1  - Photochemically induced mercuric oxide - iodine oxidation of some unsaturated steroid compounds
VL  - 50
IS  - 6
SP  - 1833
EP  - 1846
DO  - 10.1016/S0040-4020(01)80855-3
ER  - 

@article{
author = "Dabović, Milan and Bjelaković, Mira and Andrejević, V. and Lorenc, Ljubinka and Mihailović, Milhailo Lj.",
year = "1994",
abstract = "Photochemically induced HgO/I2 oxidation of cholest-5-en-3α-ol (6) and cholest-5-en-3β-ol (7) afforded (Scheme 3) products arising from the corresponding alkoxy radicals (12, 13 and 14a,b) and from attack of the I2O intermediate at the olefinic double bond (epoxides 15a and 16a,b respectively). With cholest-5-ene-1α,3β-diol 3-acetate (8) and cholest-7-ene-3β,5α-diol 3-acetate (9) the HgO/I2 oxidation led to unresolvable complex mixtures (Scheme 5). With the same reagent cholest-5-en-3α-ol acetate (10) and cholest-5-en-3β-ol acetate (11) underwent exclusively attack by I2O, to give epoxides 20a,b, iodohydrin 21, and rearranged products 19 and 22 (Scheme 7), in the case of 10, and predominantly epoxides 23a,b (Scheme 8), in the case of 11. © 1994.",
publisher = "Pergamon",
journal = "Tetrahedron",
title = "Photochemically induced mercuric oxide - iodine oxidation of some unsaturated steroid compounds",
volume = "50",
number = "6",
pages = "1833-1846",
doi = "10.1016/S0040-4020(01)80855-3"
}

Dabović, M., Bjelaković, M., Andrejević, V., Lorenc, L.,& Mihailović, M. Lj.. (1994). Photochemically induced mercuric oxide - iodine oxidation of some unsaturated steroid compounds. in Tetrahedron
Pergamon., 50(6), 1833-1846.
https://doi.org/10.1016/S0040-4020(01)80855-3

Dabović M, Bjelaković M, Andrejević V, Lorenc L, Mihailović ML. Photochemically induced mercuric oxide - iodine oxidation of some unsaturated steroid compounds. in Tetrahedron. 1994;50(6):1833-1846.
doi:10.1016/S0040-4020(01)80855-3 .

Dabović, Milan, Bjelaković, Mira, Andrejević, V., Lorenc, Ljubinka, Mihailović, Milhailo Lj., "Photochemically induced mercuric oxide - iodine oxidation of some unsaturated steroid compounds" in Tetrahedron, 50, no. 6 (1994):1833-1846,
https://doi.org/10.1016/S0040-4020(01)80855-3 . .

TY  - JOUR
AU  - Juranić, Ivan
AU  - Mihailović, Milhailo Lj.
AU  - Dabović, Milan
PY  - 1994
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2710
AB  - The reactivity of the butoxy and 3-methylcyclohexyl radicals, as representatives of alkoxy radicals, was studied by MNDO-PM3 semiempirical MO method. In both cases it was found that the oxy radical underwent easily 1,5-H migration giving a δ-hydroxyalkyl radical. The hydrogen abstraction reaction goes through two transition states. The first transition state (TS) with short O-H distance has an energy very similar to, or lower than, the TS for 1,5-H migration. The second TS is of higher energy and is much product-like. The overall cyclisation reaction has a high activation energy (over 40 kcal mol-1), and is therefore unlikely to occur spontaneously. Most likely, the cyclisation step needs assistance of some other surrounding molecules to speed up the reaction.
PB  - Royal Society of Chemistry
T2  - Journal of the Chemical Society, Perkin Transactions 2
T1  - Cyclisation of alkoxy radicals. A semiempirical MNDO-PM3 study
IS  - 4
SP  - 877
EP  - 881
UR  - https://hdl.handle.net/21.15107/rcub_cer_2710
ER  - 

@article{
author = "Juranić, Ivan and Mihailović, Milhailo Lj. and Dabović, Milan",
year = "1994",
abstract = "The reactivity of the butoxy and 3-methylcyclohexyl radicals, as representatives of alkoxy radicals, was studied by MNDO-PM3 semiempirical MO method. In both cases it was found that the oxy radical underwent easily 1,5-H migration giving a δ-hydroxyalkyl radical. The hydrogen abstraction reaction goes through two transition states. The first transition state (TS) with short O-H distance has an energy very similar to, or lower than, the TS for 1,5-H migration. The second TS is of higher energy and is much product-like. The overall cyclisation reaction has a high activation energy (over 40 kcal mol-1), and is therefore unlikely to occur spontaneously. Most likely, the cyclisation step needs assistance of some other surrounding molecules to speed up the reaction.",
publisher = "Royal Society of Chemistry",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
title = "Cyclisation of alkoxy radicals. A semiempirical MNDO-PM3 study",
number = "4",
pages = "877-881",
url = "https://hdl.handle.net/21.15107/rcub_cer_2710"
}

Juranić, I., Mihailović, M. Lj.,& Dabović, M.. (1994). Cyclisation of alkoxy radicals. A semiempirical MNDO-PM3 study. in Journal of the Chemical Society, Perkin Transactions 2
Royal Society of Chemistry.(4), 877-881.
https://hdl.handle.net/21.15107/rcub_cer_2710

Juranić I, Mihailović ML, Dabović M. Cyclisation of alkoxy radicals. A semiempirical MNDO-PM3 study. in Journal of the Chemical Society, Perkin Transactions 2. 1994;(4):877-881.
https://hdl.handle.net/21.15107/rcub_cer_2710 .

Juranić, Ivan, Mihailović, Milhailo Lj., Dabović, Milan, "Cyclisation of alkoxy radicals. A semiempirical MNDO-PM3 study" in Journal of the Chemical Society, Perkin Transactions 2, no. 4 (1994):877-881,
https://hdl.handle.net/21.15107/rcub_cer_2710 .

TY  - JOUR
AU  - Tinant, Bernard
AU  - Declercq, J P
AU  - Dabović, Milan
AU  - Krstić, Natalija
AU  - Lorenc, Ljubinka
AU  - Mihailović, Milhailo Lj.
PY  - 1993
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2704
AB  - The molecular structure of the title compound, which might be a possible intermediate in the synthesis of 5,10:8,9‐diseco‐steroids (=steroklastanes), was determined by X‐ray analysis. Hydrogen bonding between the 5α‐hydroxyl group and the 9‐oxo function attached to the ten‐membered ring, and the presence of two conformational forms of the side‐chain in the solid state structure of 2 are established. Copyright © 1993 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim
PB  - Comltb van Beheer van het Bulletin V.Z.W.
T2  - Bulletin des Sociétés Chimiques Belges
T1  - Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate
VL  - 102
IS  - 8
SP  - 539
EP  - 544
DO  - 10.1002/bscb.19931020806
ER  - 

@article{
author = "Tinant, Bernard and Declercq, J P and Dabović, Milan and Krstić, Natalija and Lorenc, Ljubinka and Mihailović, Milhailo Lj.",
year = "1993",
abstract = "The molecular structure of the title compound, which might be a possible intermediate in the synthesis of 5,10:8,9‐diseco‐steroids (=steroklastanes), was determined by X‐ray analysis. Hydrogen bonding between the 5α‐hydroxyl group and the 9‐oxo function attached to the ten‐membered ring, and the presence of two conformational forms of the side‐chain in the solid state structure of 2 are established. Copyright © 1993 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim",
publisher = "Comltb van Beheer van het Bulletin V.Z.W.",
journal = "Bulletin des Sociétés Chimiques Belges",
title = "Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate",
volume = "102",
number = "8",
pages = "539-544",
doi = "10.1002/bscb.19931020806"
}

Tinant, B., Declercq, J. P., Dabović, M., Krstić, N., Lorenc, L.,& Mihailović, M. Lj.. (1993). Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate. in Bulletin des Sociétés Chimiques Belges
Comltb van Beheer van het Bulletin V.Z.W.., 102(8), 539-544.
https://doi.org/10.1002/bscb.19931020806

Tinant B, Declercq JP, Dabović M, Krstić N, Lorenc L, Mihailović ML. Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate. in Bulletin des Sociétés Chimiques Belges. 1993;102(8):539-544.
doi:10.1002/bscb.19931020806 .

Tinant, Bernard, Declercq, J P, Dabović, Milan, Krstić, Natalija, Lorenc, Ljubinka, Mihailović, Milhailo Lj., "Crystal Structure and Solid State Conformation of 5‐Hydroxy‐8,9‐Dioxo‐8,9‐Seco‐α‐Cholestan‐3β‐yl Acetate" in Bulletin des Sociétés Chimiques Belges, 102, no. 8 (1993):539-544,
https://doi.org/10.1002/bscb.19931020806 . .

TY  - JOUR
AU  - Lorenc, Ljubinka
AU  - Juranić, Ivan
AU  - Dabović, Milan
AU  - Mihailović, Milhailo Lj.
PY  - 1991
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2698
AB  - UV irradiation of the steroidal isoxazolidines 2a, 2b, and 2c in various solvents in the presence of molecular oxygen, results in oxidative cleavage of the epoxyimino bridge to give several products; the N-unsubstituted isoxazolidine 2a afforded the nitro products 3, 4, and 5 and the azoxy compounds 6 and 7, while the N-methyl and N-acetyl derivatives 2b and 2c produced only the nitro compounds 3 and 5 as sole identifiable material. An explanation of the observed photooxygenation processes involving exciplex formation followed by proton transfer from isaxazolidine to molecular oxygen is presented. © 1991.
PB  - Pergamon press
T2  - Tetrahedron
T1  - Non-sensitized photooxygenation of some steroidal isoxazolidines
VL  - 47
IS  - 32
SP  - 6389
EP  - 6398
DO  - 10.1016/S0040-4020(01)86567-4
ER  - 

@article{
author = "Lorenc, Ljubinka and Juranić, Ivan and Dabović, Milan and Mihailović, Milhailo Lj.",
year = "1991",
abstract = "UV irradiation of the steroidal isoxazolidines 2a, 2b, and 2c in various solvents in the presence of molecular oxygen, results in oxidative cleavage of the epoxyimino bridge to give several products; the N-unsubstituted isoxazolidine 2a afforded the nitro products 3, 4, and 5 and the azoxy compounds 6 and 7, while the N-methyl and N-acetyl derivatives 2b and 2c produced only the nitro compounds 3 and 5 as sole identifiable material. An explanation of the observed photooxygenation processes involving exciplex formation followed by proton transfer from isaxazolidine to molecular oxygen is presented. © 1991.",
publisher = "Pergamon press",
journal = "Tetrahedron",
title = "Non-sensitized photooxygenation of some steroidal isoxazolidines",
volume = "47",
number = "32",
pages = "6389-6398",
doi = "10.1016/S0040-4020(01)86567-4"
}

Lorenc, L., Juranić, I., Dabović, M.,& Mihailović, M. Lj.. (1991). Non-sensitized photooxygenation of some steroidal isoxazolidines. in Tetrahedron
Pergamon press., 47(32), 6389-6398.
https://doi.org/10.1016/S0040-4020(01)86567-4

Lorenc L, Juranić I, Dabović M, Mihailović ML. Non-sensitized photooxygenation of some steroidal isoxazolidines. in Tetrahedron. 1991;47(32):6389-6398.
doi:10.1016/S0040-4020(01)86567-4 .

Lorenc, Ljubinka, Juranić, Ivan, Dabović, Milan, Mihailović, Milhailo Lj., "Non-sensitized photooxygenation of some steroidal isoxazolidines" in Tetrahedron, 47, no. 32 (1991):6389-6398,
https://doi.org/10.1016/S0040-4020(01)86567-4 . .

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Lorenc, Ljubinka
AU  - Dabović, Milan
AU  - Bjelaković, Mira
PY  - 1988
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2699
AB  - The oxidation of androst-4-ene-3β,9α,17β-triol 3,17-diacetate (2) with lead tetraacetate resulted mainly In β-fragmentation of the C(9)-C(10) bond to give a mixture of 10α- and 10β-acetoxy-Δ4-unsaturated 9,10-seco-steroidal ketones (3a and 3b) as the minor components (in ~7% yield) and the rearranged 4β-acetoxy-Δ5(10) -unsaturated 9,10-seco-9-ketone (4) as the major product (in 61% yield). Unexpectedly, when the same substrate (2) was subjected to the mercuric oxide - iodine oxidation, it underwent predominantly α-epoxidation of the olefinic double bond to produce the 4α,5α-epoxy derivative (5) (in 58% yield). © 1988.
T2  - Tetrahedron
T1  - Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate
VL  - 44
IS  - 19
SP  - 6201
EP  - 6206
DO  - 10.1016/S0040-4020(01)89810-0
ER  - 

@article{
author = "Mihailović, Milhailo Lj. and Lorenc, Ljubinka and Dabović, Milan and Bjelaković, Mira",
year = "1988",
abstract = "The oxidation of androst-4-ene-3β,9α,17β-triol 3,17-diacetate (2) with lead tetraacetate resulted mainly In β-fragmentation of the C(9)-C(10) bond to give a mixture of 10α- and 10β-acetoxy-Δ4-unsaturated 9,10-seco-steroidal ketones (3a and 3b) as the minor components (in ~7% yield) and the rearranged 4β-acetoxy-Δ5(10) -unsaturated 9,10-seco-9-ketone (4) as the major product (in 61% yield). Unexpectedly, when the same substrate (2) was subjected to the mercuric oxide - iodine oxidation, it underwent predominantly α-epoxidation of the olefinic double bond to produce the 4α,5α-epoxy derivative (5) (in 58% yield). © 1988.",
journal = "Tetrahedron",
title = "Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate",
volume = "44",
number = "19",
pages = "6201-6206",
doi = "10.1016/S0040-4020(01)89810-0"
}

Mihailović, M. Lj., Lorenc, L., Dabović, M.,& Bjelaković, M.. (1988). Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate. in Tetrahedron, 44(19), 6201-6206.
https://doi.org/10.1016/S0040-4020(01)89810-0

Mihailović ML, Lorenc L, Dabović M, Bjelaković M. Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate. in Tetrahedron. 1988;44(19):6201-6206.
doi:10.1016/S0040-4020(01)89810-0 .

Mihailović, Milhailo Lj., Lorenc, Ljubinka, Dabović, Milan, Bjelaković, Mira, "Free-radical oxidative transformations of androst-4-ene-3β,9α,17β-triol 3,17-diacetate" in Tetrahedron, 44, no. 19 (1988):6201-6206,
https://doi.org/10.1016/S0040-4020(01)89810-0 . .

TY  - JOUR
AU  - Lorenc, Ljubinka
AU  - Dabović, Milan
AU  - Juranić, Ivan
AU  - Mihailović, Milhailo Lj.
AU  - Snatzke, G
AU  - Tóth, G
PY  - 1982
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2696
AB  - Circular dichroism of the rearranged keto steroids 3 and 4, containing a condensed three and nine-membered ring system, shows that the conformation of the nine-membered ring is the same in solution as in the crystal; reduction of the kto group does not change this situation. CD also indicates that epimerization at C(5) in the pair 7 8 and the pair 11 12 leaves the cyclononanone ring conformation unchanged. © 1982.
PB  - Elsevier
T2  - Tetrahedron
T1  - Circular dichroism of some cyclopropane ring containing 1,3-cyclo-5,10-seco-steroidal ketones
VL  - 38
IS  - 21
SP  - 3163
EP  - 3168
DO  - 10.1016/0040-4020(82)80053-7
ER  - 

@article{
author = "Lorenc, Ljubinka and Dabović, Milan and Juranić, Ivan and Mihailović, Milhailo Lj. and Snatzke, G and Tóth, G",
year = "1982",
abstract = "Circular dichroism of the rearranged keto steroids 3 and 4, containing a condensed three and nine-membered ring system, shows that the conformation of the nine-membered ring is the same in solution as in the crystal; reduction of the kto group does not change this situation. CD also indicates that epimerization at C(5) in the pair 7 8 and the pair 11 12 leaves the cyclononanone ring conformation unchanged. © 1982.",
publisher = "Elsevier",
journal = "Tetrahedron",
title = "Circular dichroism of some cyclopropane ring containing 1,3-cyclo-5,10-seco-steroidal ketones",
volume = "38",
number = "21",
pages = "3163-3168",
doi = "10.1016/0040-4020(82)80053-7"
}

Lorenc, L., Dabović, M., Juranić, I., Mihailović, M. Lj., Snatzke, G.,& Tóth, G.. (1982). Circular dichroism of some cyclopropane ring containing 1,3-cyclo-5,10-seco-steroidal ketones. in Tetrahedron
Elsevier., 38(21), 3163-3168.
https://doi.org/10.1016/0040-4020(82)80053-7

Lorenc L, Dabović M, Juranić I, Mihailović ML, Snatzke G, Tóth G. Circular dichroism of some cyclopropane ring containing 1,3-cyclo-5,10-seco-steroidal ketones. in Tetrahedron. 1982;38(21):3163-3168.
doi:10.1016/0040-4020(82)80053-7 .

Lorenc, Ljubinka, Dabović, Milan, Juranić, Ivan, Mihailović, Milhailo Lj., Snatzke, G, Tóth, G, "Circular dichroism of some cyclopropane ring containing 1,3-cyclo-5,10-seco-steroidal ketones" in Tetrahedron, 38, no. 21 (1982):3163-3168,
https://doi.org/10.1016/0040-4020(82)80053-7 . .

TY  - JOUR
AU  - Lorenc, Ljubinka
AU  - Gašić, Miroslav J.
AU  - Juranić, Ivan
AU  - Dabović, Milan
AU  - Minailović, M. Lj.
PY  - 1980
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2709
AB  - Kinetic measurements of the solvolysis of (Z)-3α- and (Z)-3β-, and (E)-3α- and (E)-3β-tosyloxy-5,10-secocholest-1(10)-en-5-ones in buffered aqueous acetone (90 : 10 v/v) reveal that the (Z)-3α-, (E)-3α-, and (E)-3β-tosylates are solvolysed according to a first-order rate law (the relative rates being ca. 1 : 3 : 8), while the (Z)-3β-ester, under the same conditions, reacts at a much slower rate by a complex mechanism, the kinetics of which are best approximated by a second-order law. These data and product analysis indicate that the former three esters are solvolysed with considerable double bond participation [resulting in the case of the (E)-3-esters in intramolecular cyclopropane ring closure], and that this interaction is unimportant for the (Z)-3β-tosylate. On the basis of conformational analysis of the starting tosylates and stereoelectronic requirements for homoallylic interaction, a possible mechanistic pathway for these solvolyses is proposed.
PB  - Royal Society of Chemistry
T2  - Journal of the Chemical Society, Perkin Transactions 2
T1  - Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates
IS  - 9
SP  - 1356
EP  - 1365
UR  - https://hdl.handle.net/21.15107/rcub_cer_2709
ER  - 

@article{
author = "Lorenc, Ljubinka and Gašić, Miroslav J. and Juranić, Ivan and Dabović, Milan and Minailović, M. Lj.",
year = "1980",
abstract = "Kinetic measurements of the solvolysis of (Z)-3α- and (Z)-3β-, and (E)-3α- and (E)-3β-tosyloxy-5,10-secocholest-1(10)-en-5-ones in buffered aqueous acetone (90 : 10 v/v) reveal that the (Z)-3α-, (E)-3α-, and (E)-3β-tosylates are solvolysed according to a first-order rate law (the relative rates being ca. 1 : 3 : 8), while the (Z)-3β-ester, under the same conditions, reacts at a much slower rate by a complex mechanism, the kinetics of which are best approximated by a second-order law. These data and product analysis indicate that the former three esters are solvolysed with considerable double bond participation [resulting in the case of the (E)-3-esters in intramolecular cyclopropane ring closure], and that this interaction is unimportant for the (Z)-3β-tosylate. On the basis of conformational analysis of the starting tosylates and stereoelectronic requirements for homoallylic interaction, a possible mechanistic pathway for these solvolyses is proposed.",
publisher = "Royal Society of Chemistry",
journal = "Journal of the Chemical Society, Perkin Transactions 2",
title = "Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates",
number = "9",
pages = "1356-1365",
url = "https://hdl.handle.net/21.15107/rcub_cer_2709"
}

Lorenc, L., Gašić, M. J., Juranić, I., Dabović, M.,& Minailović, M. Lj.. (1980). Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates. in Journal of the Chemical Society, Perkin Transactions 2
Royal Society of Chemistry.(9), 1356-1365.
https://hdl.handle.net/21.15107/rcub_cer_2709

Lorenc L, Gašić MJ, Juranić I, Dabović M, Minailović ML. Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates. in Journal of the Chemical Society, Perkin Transactions 2. 1980;(9):1356-1365.
https://hdl.handle.net/21.15107/rcub_cer_2709 .

Lorenc, Ljubinka, Gašić, Miroslav J., Juranić, Ivan, Dabović, Milan, Minailović, M. Lj., "Synthesis, structure, and reactions of secosteroids containing a medium-sized ring. Part 17. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 3-tosylates" in Journal of the Chemical Society, Perkin Transactions 2, no. 9 (1980):1356-1365,
https://hdl.handle.net/21.15107/rcub_cer_2709 .

TY  - JOUR
AU  - Lorenc, Ljubinka
AU  - Gašić, Miroslav J.
AU  - Dabović, Milan
AU  - Vuletić, N
AU  - Mihailović, Milhailo Lj.
PY  - 1979
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2700
AB  - The solvolysis of (Z)- and (E)-3β-acyloxy-5,10-seco-1(10)-cholesten-5β-ol p-nitrobenzoates 4 and 5 has been investigated and compared with the solvolytic reactivity of the epimeric (Z)- and (E)-5α-p-nitrobenzoates 1 and 2, as well as of the reference compound, i.e. the 1,10-saturated 5α-p-nitrobenzoate. Kinetic data and product analysis revealed that the relative spatial orientation of the 1(10)-olefinic double bond and the chiral center at C(5) in the 10-membered ring, which these secosteroidal 5-p-nitrobenzoates can adopt in the transition state, is the main factor which determines their solvolytic behaviour, so that the esters 1,2 and 5 solvolyse with transannular double bond participation, while such an interaction is not present in the case of the (Z)-5β-ester 4. © 1979.
PB  - Pergamon Press
T2  - Tetrahedron
T2  - Tetrahedron
T1  - Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates
VL  - 35
IS  - 20
SP  - 2445
EP  - 2452
DO  - 10.1016/S0040-4020(01)93762-7
ER  - 

@article{
author = "Lorenc, Ljubinka and Gašić, Miroslav J. and Dabović, Milan and Vuletić, N and Mihailović, Milhailo Lj.",
year = "1979",
abstract = "The solvolysis of (Z)- and (E)-3β-acyloxy-5,10-seco-1(10)-cholesten-5β-ol p-nitrobenzoates 4 and 5 has been investigated and compared with the solvolytic reactivity of the epimeric (Z)- and (E)-5α-p-nitrobenzoates 1 and 2, as well as of the reference compound, i.e. the 1,10-saturated 5α-p-nitrobenzoate. Kinetic data and product analysis revealed that the relative spatial orientation of the 1(10)-olefinic double bond and the chiral center at C(5) in the 10-membered ring, which these secosteroidal 5-p-nitrobenzoates can adopt in the transition state, is the main factor which determines their solvolytic behaviour, so that the esters 1,2 and 5 solvolyse with transannular double bond participation, while such an interaction is not present in the case of the (Z)-5β-ester 4. © 1979.",
publisher = "Pergamon Press",
journal = "Tetrahedron, Tetrahedron",
title = "Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates",
volume = "35",
number = "20",
pages = "2445-2452",
doi = "10.1016/S0040-4020(01)93762-7"
}

Lorenc, L., Gašić, M. J., Dabović, M., Vuletić, N.,& Mihailović, M. Lj.. (1979). Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates. in Tetrahedron
Pergamon Press., 35(20), 2445-2452.
https://doi.org/10.1016/S0040-4020(01)93762-7

Lorenc L, Gašić MJ, Dabović M, Vuletić N, Mihailović ML. Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates. in Tetrahedron. 1979;35(20):2445-2452.
doi:10.1016/S0040-4020(01)93762-7 .

Lorenc, Ljubinka, Gašić, Miroslav J., Dabović, Milan, Vuletić, N, Mihailović, Milhailo Lj., "Structure-reactivity relationship in the solvolysis of 5,10-secosteroidal 5-p-nitrobenzoates" in Tetrahedron, 35, no. 20 (1979):2445-2452,
https://doi.org/10.1016/S0040-4020(01)93762-7 . .

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Lorenc, Ljubinka
AU  - Dabović, Milan
AU  - Juranić, Ivan
AU  - Wenkert, E.
AU  - Bernassau, J.-M.
AU  - Raju, M S
AU  - McPhail, A T
AU  - Miller, R W
PY  - 1979
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2703
AB  - The stereochemistries and conformations of the cyclopropane ring containing compounds derived from (E-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates have been determined by X-ray methods and the results correlated with 13C nmr chemical shift data. © 1979.
PB  - Pergamon Press
T2  - Tetrahedron Letters
T1  - X-ray and carbon-13 nuclear magnetic resonance characterization of cyclopropane derivatives obtained by solvolysis of (E)-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates
VL  - 20
IS  - 51
SP  - 4917
EP  - 4920
DO  - 10.1016/S0040-4039(01)86749-6
ER  - 

@article{
author = "Mihailović, Milhailo Lj. and Lorenc, Ljubinka and Dabović, Milan and Juranić, Ivan and Wenkert, E. and Bernassau, J.-M. and Raju, M S and McPhail, A T and Miller, R W",
year = "1979",
abstract = "The stereochemistries and conformations of the cyclopropane ring containing compounds derived from (E-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates have been determined by X-ray methods and the results correlated with 13C nmr chemical shift data. © 1979.",
publisher = "Pergamon Press",
journal = "Tetrahedron Letters",
title = "X-ray and carbon-13 nuclear magnetic resonance characterization of cyclopropane derivatives obtained by solvolysis of (E)-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates",
volume = "20",
number = "51",
pages = "4917-4920",
doi = "10.1016/S0040-4039(01)86749-6"
}

Mihailović, M. Lj., Lorenc, L., Dabović, M., Juranić, I., Wenkert, E., Bernassau, J.-M., Raju, M. S., McPhail, A. T.,& Miller, R. W.. (1979). X-ray and carbon-13 nuclear magnetic resonance characterization of cyclopropane derivatives obtained by solvolysis of (E)-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates. in Tetrahedron Letters
Pergamon Press., 20(51), 4917-4920.
https://doi.org/10.1016/S0040-4039(01)86749-6

Mihailović ML, Lorenc L, Dabović M, Juranić I, Wenkert E, Bernassau J, Raju MS, McPhail AT, Miller RW. X-ray and carbon-13 nuclear magnetic resonance characterization of cyclopropane derivatives obtained by solvolysis of (E)-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates. in Tetrahedron Letters. 1979;20(51):4917-4920.
doi:10.1016/S0040-4039(01)86749-6 .

Mihailović, Milhailo Lj., Lorenc, Ljubinka, Dabović, Milan, Juranić, Ivan, Wenkert, E., Bernassau, J.-M., Raju, M S, McPhail, A T, Miller, R W, "X-ray and carbon-13 nuclear magnetic resonance characterization of cyclopropane derivatives obtained by solvolysis of (E)-3α- and (E)-3β-hydroxy-5,10-seco-1(10)-cholesten-5-one tosylates" in Tetrahedron Letters, 20, no. 51 (1979):4917-4920,
https://doi.org/10.1016/S0040-4039(01)86749-6 . .

TY  - JOUR
AU  - Lorenc, Ljubinka
AU  - Gašić, Miroslav J.
AU  - Juranić, Ivan
AU  - Dabović, Milan
AU  - Mihailović, Milhailo Lj.
PY  - 1974
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2702
PB  - Pergamon Press
T2  - Tetrahedron Letters
T1  - Homoallylic interaction in steroidal cyclodecenyl systems
VL  - 15
IS  - 5
SP  - 395
EP  - 398
DO  - 10.1016/S0040-4039(01)82223-1
ER  - 

@article{
author = "Lorenc, Ljubinka and Gašić, Miroslav J. and Juranić, Ivan and Dabović, Milan and Mihailović, Milhailo Lj.",
year = "1974",
publisher = "Pergamon Press",
journal = "Tetrahedron Letters",
title = "Homoallylic interaction in steroidal cyclodecenyl systems",
volume = "15",
number = "5",
pages = "395-398",
doi = "10.1016/S0040-4039(01)82223-1"
}

Lorenc, L., Gašić, M. J., Juranić, I., Dabović, M.,& Mihailović, M. Lj.. (1974). Homoallylic interaction in steroidal cyclodecenyl systems. in Tetrahedron Letters
Pergamon Press., 15(5), 395-398.
https://doi.org/10.1016/S0040-4039(01)82223-1

Lorenc L, Gašić MJ, Juranić I, Dabović M, Mihailović ML. Homoallylic interaction in steroidal cyclodecenyl systems. in Tetrahedron Letters. 1974;15(5):395-398.
doi:10.1016/S0040-4039(01)82223-1 .

Lorenc, Ljubinka, Gašić, Miroslav J., Juranić, Ivan, Dabović, Milan, Mihailović, Milhailo Lj., "Homoallylic interaction in steroidal cyclodecenyl systems" in Tetrahedron Letters, 15, no. 5 (1974):395-398,
https://doi.org/10.1016/S0040-4039(01)82223-1 . .

TY  - JOUR
AU  - Mihailović, Milhailo Lj.
AU  - Dabović, Milan
AU  - Lorenc, Ljubinka
AU  - Gašić, Miroslav J.
PY  - 1970
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2701
PB  - Pergamon Press
T2  - Tetrahedron Letters
T1  - Transannular solvolysis reactions in seco-steroids containing a ten-membered ring.
VL  - 11
IS  - 49
SP  - 4245
EP  - 4248
DO  - 10.1016/S0040-4039(00)89455-1
ER  - 

@article{
author = "Mihailović, Milhailo Lj. and Dabović, Milan and Lorenc, Ljubinka and Gašić, Miroslav J.",
year = "1970",
publisher = "Pergamon Press",
journal = "Tetrahedron Letters",
title = "Transannular solvolysis reactions in seco-steroids containing a ten-membered ring.",
volume = "11",
number = "49",
pages = "4245-4248",
doi = "10.1016/S0040-4039(00)89455-1"
}

Mihailović, M. Lj., Dabović, M., Lorenc, L.,& Gašić, M. J.. (1970). Transannular solvolysis reactions in seco-steroids containing a ten-membered ring.. in Tetrahedron Letters
Pergamon Press., 11(49), 4245-4248.
https://doi.org/10.1016/S0040-4039(00)89455-1

Mihailović ML, Dabović M, Lorenc L, Gašić MJ. Transannular solvolysis reactions in seco-steroids containing a ten-membered ring.. in Tetrahedron Letters. 1970;11(49):4245-4248.
doi:10.1016/S0040-4039(00)89455-1 .

Mihailović, Milhailo Lj., Dabović, Milan, Lorenc, Ljubinka, Gašić, Miroslav J., "Transannular solvolysis reactions in seco-steroids containing a ten-membered ring." in Tetrahedron Letters, 11, no. 49 (1970):4245-4248,
https://doi.org/10.1016/S0040-4039(00)89455-1 . .