TY  - JOUR
AU  - Bondarenko-Gheorghiu, Lidija
AU  - Lorenc, Ljubinka
AU  - Mihailović, Milhailo Lj.
PY  - 2000
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/3500
AB  - The Diels-Alder adduct (3), obtained by cycloaddition of 7-dehydrocholesteryl
acetate (1) and maleic anhydride (2), was heated at ca. 90 oC with a large excess of lead
tetraacetate in pyridine solution for 5 h. Under these conditions, compound 3 underwent
lactonization with the participation of the olefinic D6
-double bond to give two isomeric
monolactone derivatives, 9 and 10 (in a total yield of ca. 6%), and the bislactone product
11 (in 11.5% yield). The starting material was recovered in 36% yield.
AB  - Dils-Alderov adukt 3, dobiven cikloadicijom 7-dehidroholesteril-acetata 1 i
 anhidrida maleinske kiseline 2, oksidovan je velikim viškom olovotetraacetata u
 piridinskom rastvoru na oko 90 ºC u toku 5h. Pod navedenim uslovima izvršena je
 oksidativna laktonizacija jedinjenja 3 sa participacijom olefinske D6
 -dvogube veze
 pri čemu su dobivena dva izomerna monolaktonska derivata 9 i 10 (u ukupnm prinosu od
 oko 6%) i bislaktonski proizvod 11 (u prinosu od oko 11,5%); pri tome je nepromenjen
 polazni adukt izolovan u prinosu od »36%.
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride
T1  - Olovotetraacetatna oksidacija Dils-Adlerovog adukta 7-dehidro-holesteril-acetata sa anhidridom maleinske kiseline
VL  - 65
IS  - 3
SP  - 147
EP  - 156
DO  - 10.2298/JSC0003147B
ER  - 

@article{
author = "Bondarenko-Gheorghiu, Lidija and Lorenc, Ljubinka and Mihailović, Milhailo Lj.",
year = "2000",
abstract = "The Diels-Alder adduct (3), obtained by cycloaddition of 7-dehydrocholesteryl
acetate (1) and maleic anhydride (2), was heated at ca. 90 oC with a large excess of lead
tetraacetate in pyridine solution for 5 h. Under these conditions, compound 3 underwent
lactonization with the participation of the olefinic D6
-double bond to give two isomeric
monolactone derivatives, 9 and 10 (in a total yield of ca. 6%), and the bislactone product
11 (in 11.5% yield). The starting material was recovered in 36% yield., Dils-Alderov adukt 3, dobiven cikloadicijom 7-dehidroholesteril-acetata 1 i
 anhidrida maleinske kiseline 2, oksidovan je velikim viškom olovotetraacetata u
 piridinskom rastvoru na oko 90 ºC u toku 5h. Pod navedenim uslovima izvršena je
 oksidativna laktonizacija jedinjenja 3 sa participacijom olefinske D6
 -dvogube veze
 pri čemu su dobivena dva izomerna monolaktonska derivata 9 i 10 (u ukupnm prinosu od
 oko 6%) i bislaktonski proizvod 11 (u prinosu od oko 11,5%); pri tome je nepromenjen
 polazni adukt izolovan u prinosu od »36%.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride, Olovotetraacetatna oksidacija Dils-Adlerovog adukta 7-dehidro-holesteril-acetata sa anhidridom maleinske kiseline",
volume = "65",
number = "3",
pages = "147-156",
doi = "10.2298/JSC0003147B"
}

Bondarenko-Gheorghiu, L., Lorenc, L.,& Mihailović, M. Lj.. (2000). Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride. in Journal of the Serbian Chemical Society
Belgrade : Serbian Chemical Society., 65(3), 147-156.
https://doi.org/10.2298/JSC0003147B

Bondarenko-Gheorghiu L, Lorenc L, Mihailović ML. Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride. in Journal of the Serbian Chemical Society. 2000;65(3):147-156.
doi:10.2298/JSC0003147B .

Bondarenko-Gheorghiu, Lidija, Lorenc, Ljubinka, Mihailović, Milhailo Lj., "Lead tetraacetate oxidation of the Diels-Alder adduct of 7-dehydrocholestryl acetate with maleic anhydride" in Journal of the Serbian Chemical Society, 65, no. 3 (2000):147-156,
https://doi.org/10.2298/JSC0003147B . .

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  - 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  - Lorenc, Ljubinka
AU  - Bondarenko-Gheorghiu, Lidija
AU  - Pavlović, Vladimir B.
AU  - Führer, Hermann
AU  - Kalvoda, Jaroslav
AU  - Mihailović, Milhailo Lj.
PY  - 1992
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/4743
AB  - Catalytic hydrogenation of the Δ3‐unsaturated (9R,10 R)‐ and (9S,10 S)‐epoxyenol lactones 3a, b., and 4a, b., respectively, affords, in addition to the expected saturated epoxylactones 5a, b and 7a, b, also open‐chain products, i.e. the diastereoisomeric (9R,10R)‐ and (9S,10S)‐9,10‐expoxy‐8‐oxo‐4,5‐secosteroklastan‐5‐oic acids 6a, b. and 8a, b. Alkaline hydrolysis of the lactone ring of compounds 5 and 7 and subsequent acetylation of the corresponding hydroxy derivatives give as the major products the open‐chain, diasteroisomeric (9R,10R)‐ and (9S,10S)‐4‐acetoxy‐9,10‐epoxy‐methyl esters 9a, b and 11a, b, respectively, and, but only in the androstane series, the tetrahydropyran derivatives 10a and 12a, as the minor components.
PB  - Weinheim : Wiley-VCH Verlag GmbH & Co.
T2  - Helvetica Chimica Acta
T1  - Opening of the Macrocyclic Ring in 5,10:8,9‐Disecosteroids ( = Steroklastanes)
VL  - 75
IS  - 1
SP  - 203
EP  - 209
DO  - 10.1002/hlca.19920750118
ER  - 

@article{
author = "Lorenc, Ljubinka and Bondarenko-Gheorghiu, Lidija and Pavlović, Vladimir B. and Führer, Hermann and Kalvoda, Jaroslav and Mihailović, Milhailo Lj.",
year = "1992",
abstract = "Catalytic hydrogenation of the Δ3‐unsaturated (9R,10 R)‐ and (9S,10 S)‐epoxyenol lactones 3a, b., and 4a, b., respectively, affords, in addition to the expected saturated epoxylactones 5a, b and 7a, b, also open‐chain products, i.e. the diastereoisomeric (9R,10R)‐ and (9S,10S)‐9,10‐expoxy‐8‐oxo‐4,5‐secosteroklastan‐5‐oic acids 6a, b. and 8a, b. Alkaline hydrolysis of the lactone ring of compounds 5 and 7 and subsequent acetylation of the corresponding hydroxy derivatives give as the major products the open‐chain, diasteroisomeric (9R,10R)‐ and (9S,10S)‐4‐acetoxy‐9,10‐epoxy‐methyl esters 9a, b and 11a, b, respectively, and, but only in the androstane series, the tetrahydropyran derivatives 10a and 12a, as the minor components.",
publisher = "Weinheim : Wiley-VCH Verlag GmbH & Co.",
journal = "Helvetica Chimica Acta",
title = "Opening of the Macrocyclic Ring in 5,10:8,9‐Disecosteroids ( = Steroklastanes)",
volume = "75",
number = "1",
pages = "203-209",
doi = "10.1002/hlca.19920750118"
}

Lorenc, L., Bondarenko-Gheorghiu, L., Pavlović, V. B., Führer, H., Kalvoda, J.,& Mihailović, M. Lj.. (1992). Opening of the Macrocyclic Ring in 5,10:8,9‐Disecosteroids ( = Steroklastanes). in Helvetica Chimica Acta
Weinheim : Wiley-VCH Verlag GmbH & Co.., 75(1), 203-209.
https://doi.org/10.1002/hlca.19920750118

Lorenc L, Bondarenko-Gheorghiu L, Pavlović VB, Führer H, Kalvoda J, Mihailović ML. Opening of the Macrocyclic Ring in 5,10:8,9‐Disecosteroids ( = Steroklastanes). in Helvetica Chimica Acta. 1992;75(1):203-209.
doi:10.1002/hlca.19920750118 .

Lorenc, Ljubinka, Bondarenko-Gheorghiu, Lidija, Pavlović, Vladimir B., Führer, Hermann, Kalvoda, Jaroslav, Mihailović, Milhailo Lj., "Opening of the Macrocyclic Ring in 5,10:8,9‐Disecosteroids ( = Steroklastanes)" in Helvetica Chimica Acta, 75, no. 1 (1992):203-209,
https://doi.org/10.1002/hlca.19920750118 . .