The development of new synthetic methods and their application in the synthesis of natural products and biologically active molecules

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The development of new synthetic methods and their application in the synthesis of natural products and biologically active molecules (en)
Развој нових синтетичких метода и њихова примена у синтези природних производа и биолошки активних једињења (sr)
Razvoj novih sintetičkih metoda i njihova primena u sintezi prirodnih proizvoda i biološki aktivnih jedinjenja (sr_RS)
Authors

Publications

Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation

Vulović, Bojan; Trmčić, Milena; Matović, Radomir; Saičić, Radomir N.

(American Chemical Society (ACS), 2019)

TY  - JOUR
AU  - Vulović, Bojan
AU  - Trmčić, Milena
AU  - Matović, Radomir
AU  - Saičić, Radomir N.
PY  - 2019
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/3819
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3388
AB  - Unsaturated oxyallyl cations with a suitably positioned alkene bond undergo 5-exo-cyclization with the formation of vinylcyclopentane derivatives. Alkyne analogues provide allenes. The reaction proceeds with a moderate to excellent level of stereoselectivity and allows for asymmetric induction in the reaction with chiral substrate.
PB  - American Chemical Society (ACS)
T2  - Organic Letters
T1  - Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation
VL  - 21
IS  - 23
SP  - 9618
EP  - 9621
DO  - 10.1021/acs.orglett.9b03791
ER  - 
@article{
author = "Vulović, Bojan and Trmčić, Milena and Matović, Radomir and Saičić, Radomir N.",
year = "2019",
abstract = "Unsaturated oxyallyl cations with a suitably positioned alkene bond undergo 5-exo-cyclization with the formation of vinylcyclopentane derivatives. Alkyne analogues provide allenes. The reaction proceeds with a moderate to excellent level of stereoselectivity and allows for asymmetric induction in the reaction with chiral substrate.",
publisher = "American Chemical Society (ACS)",
journal = "Organic Letters",
title = "Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation",
volume = "21",
number = "23",
pages = "9618-9621",
doi = "10.1021/acs.orglett.9b03791"
}
Vulović, B., Trmčić, M., Matović, R.,& Saičić, R. N.. (2019). Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation. in Organic Letters
American Chemical Society (ACS)., 21(23), 9618-9621.
https://doi.org/10.1021/acs.orglett.9b03791
Vulović B, Trmčić M, Matović R, Saičić RN. Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation. in Organic Letters. 2019;21(23):9618-9621.
doi:10.1021/acs.orglett.9b03791 .
Vulović, Bojan, Trmčić, Milena, Matović, Radomir, Saičić, Radomir N., "Cyclization Reactions of Oxyallyl Cation. A Method for Cyclopentane Ring Formation" in Organic Letters, 21, no. 23 (2019):9618-9621,
https://doi.org/10.1021/acs.orglett.9b03791 . .
5
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Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H

Vulović, Bojan; Kolarski, Dusan; Bihelović, Filip; Matović, Radomir; Gruden, Maja; Saičić, Radomir N.

(American Chemical Society (ACS), 2016)

TY  - JOUR
AU  - Vulović, Bojan
AU  - Kolarski, Dusan
AU  - Bihelović, Filip
AU  - Matović, Radomir
AU  - Gruden, Maja
AU  - Saičić, Radomir N.
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1847
AB  - 1,6-Diynes with a t-butylcarbonate group in the propargylic position undergo gold(I)-catalyzed dominocyclization which affords alpha-hydroxycyclohexenones. The described sequence can be applied on functionalized, highly oxygenated substrates, as examplified in the synthesis of (-)-gabosine H and its epimer.
PB  - American Chemical Society (ACS)
T2  - Organic Letters
T1  - Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H
VL  - 18
IS  - 15
SP  - 3886
EP  - 3889
DO  - 10.1021/acs.orglett.6b01898
ER  - 
@article{
author = "Vulović, Bojan and Kolarski, Dusan and Bihelović, Filip and Matović, Radomir and Gruden, Maja and Saičić, Radomir N.",
year = "2016",
abstract = "1,6-Diynes with a t-butylcarbonate group in the propargylic position undergo gold(I)-catalyzed dominocyclization which affords alpha-hydroxycyclohexenones. The described sequence can be applied on functionalized, highly oxygenated substrates, as examplified in the synthesis of (-)-gabosine H and its epimer.",
publisher = "American Chemical Society (ACS)",
journal = "Organic Letters",
title = "Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H",
volume = "18",
number = "15",
pages = "3886-3889",
doi = "10.1021/acs.orglett.6b01898"
}
Vulović, B., Kolarski, D., Bihelović, F., Matović, R., Gruden, M.,& Saičić, R. N.. (2016). Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H. in Organic Letters
American Chemical Society (ACS)., 18(15), 3886-3889.
https://doi.org/10.1021/acs.orglett.6b01898
Vulović B, Kolarski D, Bihelović F, Matović R, Gruden M, Saičić RN. Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H. in Organic Letters. 2016;18(15):3886-3889.
doi:10.1021/acs.orglett.6b01898 .
Vulović, Bojan, Kolarski, Dusan, Bihelović, Filip, Matović, Radomir, Gruden, Maja, Saičić, Radomir N., "Gold(I)-Catalyzed Domino Cyclizations of Diynes for the Synthesis of Functionalized Cyclohexenone Derivatives. Total Synthesis of (-)-Gabosine H and (-)-6-epi-Gabosine H" in Organic Letters, 18, no. 15 (2016):3886-3889,
https://doi.org/10.1021/acs.orglett.6b01898 . .
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17
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18

Synthesis of vinyldihydropyran by cooperative catalysis

Vulović, Bojan; Maric, Ivana; Matović, Radomir; Saičić, Radomir N.

(Serbian Chemical Soc, Belgrade, 2016)

TY  - JOUR
AU  - Vulović, Bojan
AU  - Maric, Ivana
AU  - Matović, Radomir
AU  - Saičić, Radomir N.
PY  - 2016
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2050
AB  - Delta(5)-Unsaturated aldehydes with a suitably positioned allylic halide, or phosphate, leaving group undergo doubly-catalyzed cyclization to give dihydropyran derivatives. The cyclization proceeds under the synergetic action of diazabicycloundecene and Pd(PPh3)(4). This type of transformation was also accomplished with an aryl ketone.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis of vinyldihydropyran by cooperative catalysis
VL  - 81
IS  - 12
SP  - 1335
EP  - 1343
DO  - 10.2298/JSC161102103V
ER  - 
@article{
author = "Vulović, Bojan and Maric, Ivana and Matović, Radomir and Saičić, Radomir N.",
year = "2016",
abstract = "Delta(5)-Unsaturated aldehydes with a suitably positioned allylic halide, or phosphate, leaving group undergo doubly-catalyzed cyclization to give dihydropyran derivatives. The cyclization proceeds under the synergetic action of diazabicycloundecene and Pd(PPh3)(4). This type of transformation was also accomplished with an aryl ketone.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis of vinyldihydropyran by cooperative catalysis",
volume = "81",
number = "12",
pages = "1335-1343",
doi = "10.2298/JSC161102103V"
}
Vulović, B., Maric, I., Matović, R.,& Saičić, R. N.. (2016). Synthesis of vinyldihydropyran by cooperative catalysis. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 81(12), 1335-1343.
https://doi.org/10.2298/JSC161102103V
Vulović B, Maric I, Matović R, Saičić RN. Synthesis of vinyldihydropyran by cooperative catalysis. in Journal of the Serbian Chemical Society. 2016;81(12):1335-1343.
doi:10.2298/JSC161102103V .
Vulović, Bojan, Maric, Ivana, Matović, Radomir, Saičić, Radomir N., "Synthesis of vinyldihydropyran by cooperative catalysis" in Journal of the Serbian Chemical Society, 81, no. 12 (2016):1335-1343,
https://doi.org/10.2298/JSC161102103V . .
1
1
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Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen

Novkovic, L; Trmcic, M; Rodić, Marko V.; Bihelović, Filip; Zlatar, Matija; Matović, Radomir; Saičić, Radomir N.

(Royal Soc Chemistry, Cambridge, 2015)

TY  - JOUR
AU  - Novkovic, L
AU  - Trmcic, M
AU  - Rodić, Marko V.
AU  - Bihelović, Filip
AU  - Zlatar, Matija
AU  - Matović, Radomir
AU  - Saičić, Radomir N.
PY  - 2015
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1796
AB  - Domino reactions of ketones with molecular oxygen in the presence of potassium hydroxide and potassium t-butoxide afford cyclic hydroperoxy acetals (3,5-dihydroxy-1,2-dioxanes). Mixed endoperoxides can also be obtained in a three-component reaction of two ketones and oxygen.
PB  - Royal Soc Chemistry, Cambridge
T2  - RSC Advances
T1  - Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen
VL  - 5
IS  - 120
SP  - 99577
EP  - 99584
DO  - 10.1039/c5ra13476e
ER  - 
@article{
author = "Novkovic, L and Trmcic, M and Rodić, Marko V. and Bihelović, Filip and Zlatar, Matija and Matović, Radomir and Saičić, Radomir N.",
year = "2015",
abstract = "Domino reactions of ketones with molecular oxygen in the presence of potassium hydroxide and potassium t-butoxide afford cyclic hydroperoxy acetals (3,5-dihydroxy-1,2-dioxanes). Mixed endoperoxides can also be obtained in a three-component reaction of two ketones and oxygen.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "RSC Advances",
title = "Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen",
volume = "5",
number = "120",
pages = "99577-99584",
doi = "10.1039/c5ra13476e"
}
Novkovic, L., Trmcic, M., Rodić, M. V., Bihelović, F., Zlatar, M., Matović, R.,& Saičić, R. N.. (2015). Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen. in RSC Advances
Royal Soc Chemistry, Cambridge., 5(120), 99577-99584.
https://doi.org/10.1039/c5ra13476e
Novkovic L, Trmcic M, Rodić MV, Bihelović F, Zlatar M, Matović R, Saičić RN. Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen. in RSC Advances. 2015;5(120):99577-99584.
doi:10.1039/c5ra13476e .
Novkovic, L, Trmcic, M, Rodić, Marko V., Bihelović, Filip, Zlatar, Matija, Matović, Radomir, Saičić, Radomir N., "Synthesis of endoperoxides by domino reactions of ketones and molecular oxygen" in RSC Advances, 5, no. 120 (2015):99577-99584,
https://doi.org/10.1039/c5ra13476e . .
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Total synthesis and biological evaluation of atrop-O-benzyl-desmethylabyssomicin C

Matović, Radomir; Bihelović, Filip; Gruden-Pavlović, Maja; Saičić, Radomir N.

(Royal Soc Chemistry, Cambridge, 2014)

TY  - JOUR
AU  - Matović, Radomir
AU  - Bihelović, Filip
AU  - Gruden-Pavlović, Maja
AU  - Saičić, Radomir N.
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1400
AB  - The total synthesis of desmethylabyssomicin C analogue 1 was accomplished using diastereotopos-selective ring closing metathesis and Nozaki-Hiyama-Kishi cyclization as the key steps. The synthetic analogue retained its antibacterial activity against methicillin-resistant S. aureus strains, whereas its cytotoxicity decreased for three orders of magnitude, as compared to atrop-abyssomicin C.
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic & Biomolecular Chemistry
T1  - Total synthesis and biological evaluation of atrop-O-benzyl-desmethylabyssomicin C
VL  - 12
IS  - 39
SP  - 7682
EP  - 7685
DO  - 10.1039/c4ob01436g
ER  - 
@article{
author = "Matović, Radomir and Bihelović, Filip and Gruden-Pavlović, Maja and Saičić, Radomir N.",
year = "2014",
abstract = "The total synthesis of desmethylabyssomicin C analogue 1 was accomplished using diastereotopos-selective ring closing metathesis and Nozaki-Hiyama-Kishi cyclization as the key steps. The synthetic analogue retained its antibacterial activity against methicillin-resistant S. aureus strains, whereas its cytotoxicity decreased for three orders of magnitude, as compared to atrop-abyssomicin C.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic & Biomolecular Chemistry",
title = "Total synthesis and biological evaluation of atrop-O-benzyl-desmethylabyssomicin C",
volume = "12",
number = "39",
pages = "7682-7685",
doi = "10.1039/c4ob01436g"
}
Matović, R., Bihelović, F., Gruden-Pavlović, M.,& Saičić, R. N.. (2014). Total synthesis and biological evaluation of atrop-O-benzyl-desmethylabyssomicin C. in Organic & Biomolecular Chemistry
Royal Soc Chemistry, Cambridge., 12(39), 7682-7685.
https://doi.org/10.1039/c4ob01436g
Matović R, Bihelović F, Gruden-Pavlović M, Saičić RN. Total synthesis and biological evaluation of atrop-O-benzyl-desmethylabyssomicin C. in Organic & Biomolecular Chemistry. 2014;12(39):7682-7685.
doi:10.1039/c4ob01436g .
Matović, Radomir, Bihelović, Filip, Gruden-Pavlović, Maja, Saičić, Radomir N., "Total synthesis and biological evaluation of atrop-O-benzyl-desmethylabyssomicin C" in Organic & Biomolecular Chemistry, 12, no. 39 (2014):7682-7685,
https://doi.org/10.1039/c4ob01436g . .
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12
12

Substrate Stereocontrol in the Intramolecular Organocatalyzed Tsuji-Trost Reaction: Enantioselective Synthesis of Allokainates

Vulović, Bojan; Gruden-Pavlović, Maja; Matović, Radomir; Saičić, Radomir N.

(American Chemical Society (ACS), 2014)

TY  - JOUR
AU  - Vulović, Bojan
AU  - Gruden-Pavlović, Maja
AU  - Matović, Radomir
AU  - Saičić, Radomir N.
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1524
AB  - Organocatalyzed Tsuji-Trost cyclization of 3b proceeds with asymmetric induction and allows for stereoselective synthesis of (+)-allokainic acid. The stereochemical outcome of the cyclization was predicted by calculations.
PB  - American Chemical Society (ACS)
T2  - Organic Letters
T1  - Substrate Stereocontrol in the Intramolecular Organocatalyzed Tsuji-Trost Reaction: Enantioselective Synthesis of Allokainates
VL  - 16
IS  - 1
SP  - 34
EP  - 37
DO  - 10.1021/ol4028557
ER  - 
@article{
author = "Vulović, Bojan and Gruden-Pavlović, Maja and Matović, Radomir and Saičić, Radomir N.",
year = "2014",
abstract = "Organocatalyzed Tsuji-Trost cyclization of 3b proceeds with asymmetric induction and allows for stereoselective synthesis of (+)-allokainic acid. The stereochemical outcome of the cyclization was predicted by calculations.",
publisher = "American Chemical Society (ACS)",
journal = "Organic Letters",
title = "Substrate Stereocontrol in the Intramolecular Organocatalyzed Tsuji-Trost Reaction: Enantioselective Synthesis of Allokainates",
volume = "16",
number = "1",
pages = "34-37",
doi = "10.1021/ol4028557"
}
Vulović, B., Gruden-Pavlović, M., Matović, R.,& Saičić, R. N.. (2014). Substrate Stereocontrol in the Intramolecular Organocatalyzed Tsuji-Trost Reaction: Enantioselective Synthesis of Allokainates. in Organic Letters
American Chemical Society (ACS)., 16(1), 34-37.
https://doi.org/10.1021/ol4028557
Vulović B, Gruden-Pavlović M, Matović R, Saičić RN. Substrate Stereocontrol in the Intramolecular Organocatalyzed Tsuji-Trost Reaction: Enantioselective Synthesis of Allokainates. in Organic Letters. 2014;16(1):34-37.
doi:10.1021/ol4028557 .
Vulović, Bojan, Gruden-Pavlović, Maja, Matović, Radomir, Saičić, Radomir N., "Substrate Stereocontrol in the Intramolecular Organocatalyzed Tsuji-Trost Reaction: Enantioselective Synthesis of Allokainates" in Organic Letters, 16, no. 1 (2014):34-37,
https://doi.org/10.1021/ol4028557 . .
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Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides

Ferjančić, Zorana; Matović, Radomir; Bihelović, Filip

(Serbian Chemical Soc, Belgrade, 2014)

TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Matović, Radomir
AU  - Bihelović, Filip
PY  - 2014
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1557
AB  - Intermolecular Nozaki-Hiyama-Kishi coupling between alkenylchromium(III) reagents, derived from either (E)-(2-bromoethenyl)benzene or (E)-1-iodo-1-pentadecene, and the conformationally rigid Garner's aldehyde resulted in the stereoselective formation of Felkin-type allylic alcohols in good yields, thus providing an easy access to sphingosines. In addition, when the protecting group in the Garner's aldehyde was changed (from Boc to N-octanoyl), a reversal of stereoselectivity was observed in the reaction with (E)-1-pentadecenylchromium(III), probably as the result of hydrophobic interactions between the long carbon chains of the reaction partners.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides
VL  - 79
IS  - 6
SP  - 627
EP  - 636
DO  - 10.2298/JSC130611067F
ER  - 
@article{
author = "Ferjančić, Zorana and Matović, Radomir and Bihelović, Filip",
year = "2014",
abstract = "Intermolecular Nozaki-Hiyama-Kishi coupling between alkenylchromium(III) reagents, derived from either (E)-(2-bromoethenyl)benzene or (E)-1-iodo-1-pentadecene, and the conformationally rigid Garner's aldehyde resulted in the stereoselective formation of Felkin-type allylic alcohols in good yields, thus providing an easy access to sphingosines. In addition, when the protecting group in the Garner's aldehyde was changed (from Boc to N-octanoyl), a reversal of stereoselectivity was observed in the reaction with (E)-1-pentadecenylchromium(III), probably as the result of hydrophobic interactions between the long carbon chains of the reaction partners.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides",
volume = "79",
number = "6",
pages = "627-636",
doi = "10.2298/JSC130611067F"
}
Ferjančić, Z., Matović, R.,& Bihelović, F.. (2014). Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 79(6), 627-636.
https://doi.org/10.2298/JSC130611067F
Ferjančić Z, Matović R, Bihelović F. Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides. in Journal of the Serbian Chemical Society. 2014;79(6):627-636.
doi:10.2298/JSC130611067F .
Ferjančić, Zorana, Matović, Radomir, Bihelović, Filip, "Diastereoselective addition of alkenylchromium(III) reagents to Garner's aldehyde. The Nozaki-Hiyama-Kishi coupling approach to sphingosines and ceramides" in Journal of the Serbian Chemical Society, 79, no. 6 (2014):627-636,
https://doi.org/10.2298/JSC130611067F . .
2
2
2

Total synthesis and biological evaluation of (-)-atrop-abyssomicin C

Bihelović, Filip; Karadžić, Ivanka; Matović, Radomir; Saičić, Radomir N.

(Royal Soc Chemistry, Cambridge, 2013)

TY  - JOUR
AU  - Bihelović, Filip
AU  - Karadžić, Ivanka
AU  - Matović, Radomir
AU  - Saičić, Radomir N.
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1214
AB  - Enantioselective synthesis of a marine antibiotic (-)-atrop-abyssomicin C was accomplished in 21 steps, in 1.8% overall yield (4%, based on the recovered starting material). The key steps of the synthesis are the formation of the functionalized cyclohexane core by an organocatalyzed Tsuji-Trost reaction, the formation of a tricyclic spirotetronate unit by a gold-catalyzed reaction sequence and the highly efficient eleven-membered ring closure by a Nozaki-Hiyama-Kishi reaction. Biological tests showed all abyssomicin derivatives to possess strong antibacterial activity against methicillin resistant S. aureus strains; however, they also proved to be cytotoxic, both to malignant and to normal somatic cells.
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic & Biomolecular Chemistry
T1  - Total synthesis and biological evaluation of (-)-atrop-abyssomicin C
VL  - 11
IS  - 33
SP  - 5413
EP  - 5424
DO  - 10.1039/c3ob40692j
ER  - 
@article{
author = "Bihelović, Filip and Karadžić, Ivanka and Matović, Radomir and Saičić, Radomir N.",
year = "2013",
abstract = "Enantioselective synthesis of a marine antibiotic (-)-atrop-abyssomicin C was accomplished in 21 steps, in 1.8% overall yield (4%, based on the recovered starting material). The key steps of the synthesis are the formation of the functionalized cyclohexane core by an organocatalyzed Tsuji-Trost reaction, the formation of a tricyclic spirotetronate unit by a gold-catalyzed reaction sequence and the highly efficient eleven-membered ring closure by a Nozaki-Hiyama-Kishi reaction. Biological tests showed all abyssomicin derivatives to possess strong antibacterial activity against methicillin resistant S. aureus strains; however, they also proved to be cytotoxic, both to malignant and to normal somatic cells.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic & Biomolecular Chemistry",
title = "Total synthesis and biological evaluation of (-)-atrop-abyssomicin C",
volume = "11",
number = "33",
pages = "5413-5424",
doi = "10.1039/c3ob40692j"
}
Bihelović, F., Karadžić, I., Matović, R.,& Saičić, R. N.. (2013). Total synthesis and biological evaluation of (-)-atrop-abyssomicin C. in Organic & Biomolecular Chemistry
Royal Soc Chemistry, Cambridge., 11(33), 5413-5424.
https://doi.org/10.1039/c3ob40692j
Bihelović F, Karadžić I, Matović R, Saičić RN. Total synthesis and biological evaluation of (-)-atrop-abyssomicin C. in Organic & Biomolecular Chemistry. 2013;11(33):5413-5424.
doi:10.1039/c3ob40692j .
Bihelović, Filip, Karadžić, Ivanka, Matović, Radomir, Saičić, Radomir N., "Total synthesis and biological evaluation of (-)-atrop-abyssomicin C" in Organic & Biomolecular Chemistry, 11, no. 33 (2013):5413-5424,
https://doi.org/10.1039/c3ob40692j . .
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Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)

Marjanovic, Jasna; Divjakovic, Vladimir; Matović, Radomir; Ferjančić, Zorana; Saičić, Radomir N.

(Wiley-V C H Verlag Gmbh, Weinheim, 2013)

TY  - JOUR
AU  - Marjanovic, Jasna
AU  - Divjakovic, Vladimir
AU  - Matović, Radomir
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir N.
PY  - 2013
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1215
AB  - The stereodivergent synthesis of two hyacinthacine analogues, which relies on an organocatalyzed aldol addition, is described. The aldol addition of dioxanone to an -N-carbobenzyloxy-substituted chiral aldehyde, promoted by both (R)- and (S)-proline, proceeds in reasonable yields with acceptable diastereomeric ratios. The success of the reaction may be due to the use of an acyclic aldehyde acceptor, which allows reagent control of the stereochemical outcome of the key aldolization step in both the matched and mismatched cases.
PB  - Wiley-V C H Verlag Gmbh, Weinheim
T2  - European Journal of Organic Chemistry
T1  - Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)
VL  - 2013
IS  - 25
SP  - 5555
EP  - 5560
DO  - 10.1002/ejoc.201300716
ER  - 
@article{
author = "Marjanovic, Jasna and Divjakovic, Vladimir and Matović, Radomir and Ferjančić, Zorana and Saičić, Radomir N.",
year = "2013",
abstract = "The stereodivergent synthesis of two hyacinthacine analogues, which relies on an organocatalyzed aldol addition, is described. The aldol addition of dioxanone to an -N-carbobenzyloxy-substituted chiral aldehyde, promoted by both (R)- and (S)-proline, proceeds in reasonable yields with acceptable diastereomeric ratios. The success of the reaction may be due to the use of an acyclic aldehyde acceptor, which allows reagent control of the stereochemical outcome of the key aldolization step in both the matched and mismatched cases.",
publisher = "Wiley-V C H Verlag Gmbh, Weinheim",
journal = "European Journal of Organic Chemistry",
title = "Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)",
volume = "2013",
number = "25",
pages = "5555-5560",
doi = "10.1002/ejoc.201300716"
}
Marjanovic, J., Divjakovic, V., Matović, R., Ferjančić, Z.,& Saičić, R. N.. (2013). Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1). in European Journal of Organic Chemistry
Wiley-V C H Verlag Gmbh, Weinheim., 2013(25), 5555-5560.
https://doi.org/10.1002/ejoc.201300716
Marjanovic J, Divjakovic V, Matović R, Ferjančić Z, Saičić RN. Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1). in European Journal of Organic Chemistry. 2013;2013(25):5555-5560.
doi:10.1002/ejoc.201300716 .
Marjanovic, Jasna, Divjakovic, Vladimir, Matović, Radomir, Ferjančić, Zorana, Saičić, Radomir N., "Double Asymmetric Induction in Organocatalyzed Aldol Reactions: Total Synthesis of (+)-2-epi-Hyacinthacine A(2) and (-)-3-epi-Hyacinthacine A(1)" in European Journal of Organic Chemistry, 2013, no. 25 (2013):5555-5560,
https://doi.org/10.1002/ejoc.201300716 . .
1
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21

A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids

Trmcic, Milena V.; Matović, Radomir; Tovilović, Gordana; Ristic, Biljana Z.; Trajković, Vladimir; Ferjančić, Zorana; Saičić, Radomir N.

(Royal Soc Chemistry, Cambridge, 2012)

TY  - JOUR
AU  - Trmcic, Milena V.
AU  - Matović, Radomir
AU  - Tovilović, Gordana
AU  - Ristic, Biljana Z.
AU  - Trajković, Vladimir
AU  - Ferjančić, Zorana
AU  - Saičić, Radomir N.
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/981
AB  - The design, synthesis and biological evaluation of a novel C, D-spirolactone analogue of paclitaxel is described. This is the first paclitaxel analogue without an oxetane D-ring that shows a significant cytotoxic effect (activity one order of magnitude lower than paclitaxel). More importantly, its cytotoxicity is a result of a different mechanism of action, involving mTOR inhibition-dependent autophagy instead of G(2)/M cell cycle arrest-dependent apoptosis.
PB  - Royal Soc Chemistry, Cambridge
T2  - Organic & Biomolecular Chemistry
T1  - A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids
VL  - 10
IS  - 25
SP  - 4933
EP  - 4942
DO  - 10.1039/c2ob25514f
ER  - 
@article{
author = "Trmcic, Milena V. and Matović, Radomir and Tovilović, Gordana and Ristic, Biljana Z. and Trajković, Vladimir and Ferjančić, Zorana and Saičić, Radomir N.",
year = "2012",
abstract = "The design, synthesis and biological evaluation of a novel C, D-spirolactone analogue of paclitaxel is described. This is the first paclitaxel analogue without an oxetane D-ring that shows a significant cytotoxic effect (activity one order of magnitude lower than paclitaxel). More importantly, its cytotoxicity is a result of a different mechanism of action, involving mTOR inhibition-dependent autophagy instead of G(2)/M cell cycle arrest-dependent apoptosis.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Organic & Biomolecular Chemistry",
title = "A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids",
volume = "10",
number = "25",
pages = "4933-4942",
doi = "10.1039/c2ob25514f"
}
Trmcic, M. V., Matović, R., Tovilović, G., Ristic, B. Z., Trajković, V., Ferjančić, Z.,& Saičić, R. N.. (2012). A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids. in Organic & Biomolecular Chemistry
Royal Soc Chemistry, Cambridge., 10(25), 4933-4942.
https://doi.org/10.1039/c2ob25514f
Trmcic MV, Matović R, Tovilović G, Ristic BZ, Trajković V, Ferjančić Z, Saičić RN. A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids. in Organic & Biomolecular Chemistry. 2012;10(25):4933-4942.
doi:10.1039/c2ob25514f .
Trmcic, Milena V., Matović, Radomir, Tovilović, Gordana, Ristic, Biljana Z., Trajković, Vladimir, Ferjančić, Zorana, Saičić, Radomir N., "A novel C,D-spirolactone analogue of paclitaxel: autophagy instead of apoptosis as a previously unknown mechanism of cytotoxic action for taxoids" in Organic & Biomolecular Chemistry, 10, no. 25 (2012):4933-4942,
https://doi.org/10.1039/c2ob25514f . .
12
12
14

Synthetic studies towards D-modified paclitaxel analogues

Ferjančić, Zorana; Matović, Radomir; Saičić, Radomir N.

(Serbian Chemical Soc, Belgrade, 2012)

TY  - JOUR
AU  - Ferjančić, Zorana
AU  - Matović, Radomir
AU  - Saičić, Radomir N.
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/1056
AB  - A synthetic sequence has been developed for the preparation of 9,10- di-O-diacetyl-4-desmethylene-4β-(3-butenyl)-4α-hydroxy-5-O-mesyltaxicin I- -1,2-carbonate 3, an intermediate in an attempted synthesis of a cyclobutane paclitaxel analogue. A series of reactions of 3 were investigated, including the protection of the sterically hindered C-4α-hydroxy group and the oxidative cleavage of the terminal double bond. Cyclization of 13 to the cyclobutane-containing intermediate failed due to the unexpected instability of the dimethylsilane protecting group under basic conditions.
AB  - Razvijena je sintetička sekvenca za dobijanje 9,10-di-O-acetil-4-desmetilen-4β-(3-butenil)-4α-hidroksi-5-O-meziltaksicin I-1,2-karbonata (3), intermedijera u pokušanoj sintezi ciklobutanskog analoga paklitaksela. Ispitivana je mogućnost dalje hemijske transformacije jedinjenja 3, kao što je zaštita sterno izrazito zaštićene C-4α hidroksilne grupe i oksidativna fragmentacija terminalne dvostruke veze. Ciklizacija jedinjenja 13 nije dala željeni rezultat - intermedijer sa ciklobutanovim prstenom, što je posledica neočekivane nestabilnosti DMS-zaštitne grupe u baznim reakcionim uslovima.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Synthetic studies towards D-modified paclitaxel analogues
T1  - Sintetičke studije analoga paklitaksela sa modifikovanim D-prstenom
VL  - 77
IS  - 11
SP  - 1529
EP  - 1539
DO  - 10.2298/JSC120626094F
ER  - 
@article{
author = "Ferjančić, Zorana and Matović, Radomir and Saičić, Radomir N.",
year = "2012",
abstract = "A synthetic sequence has been developed for the preparation of 9,10- di-O-diacetyl-4-desmethylene-4β-(3-butenyl)-4α-hydroxy-5-O-mesyltaxicin I- -1,2-carbonate 3, an intermediate in an attempted synthesis of a cyclobutane paclitaxel analogue. A series of reactions of 3 were investigated, including the protection of the sterically hindered C-4α-hydroxy group and the oxidative cleavage of the terminal double bond. Cyclization of 13 to the cyclobutane-containing intermediate failed due to the unexpected instability of the dimethylsilane protecting group under basic conditions., Razvijena je sintetička sekvenca za dobijanje 9,10-di-O-acetil-4-desmetilen-4β-(3-butenil)-4α-hidroksi-5-O-meziltaksicin I-1,2-karbonata (3), intermedijera u pokušanoj sintezi ciklobutanskog analoga paklitaksela. Ispitivana je mogućnost dalje hemijske transformacije jedinjenja 3, kao što je zaštita sterno izrazito zaštićene C-4α hidroksilne grupe i oksidativna fragmentacija terminalne dvostruke veze. Ciklizacija jedinjenja 13 nije dala željeni rezultat - intermedijer sa ciklobutanovim prstenom, što je posledica neočekivane nestabilnosti DMS-zaštitne grupe u baznim reakcionim uslovima.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Synthetic studies towards D-modified paclitaxel analogues, Sintetičke studije analoga paklitaksela sa modifikovanim D-prstenom",
volume = "77",
number = "11",
pages = "1529-1539",
doi = "10.2298/JSC120626094F"
}
Ferjančić, Z., Matović, R.,& Saičić, R. N.. (2012). Synthetic studies towards D-modified paclitaxel analogues. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 77(11), 1529-1539.
https://doi.org/10.2298/JSC120626094F
Ferjančić Z, Matović R, Saičić RN. Synthetic studies towards D-modified paclitaxel analogues. in Journal of the Serbian Chemical Society. 2012;77(11):1529-1539.
doi:10.2298/JSC120626094F .
Ferjančić, Zorana, Matović, Radomir, Saičić, Radomir N., "Synthetic studies towards D-modified paclitaxel analogues" in Journal of the Serbian Chemical Society, 77, no. 11 (2012):1529-1539,
https://doi.org/10.2298/JSC120626094F . .