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Opening of the Macrocyclic Ring in 5,10:8,9‐Disecosteroids ( = Steroklastanes)

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1992
Authors
Lorenc, Ljubinka
Bondarenko-Gheorghiu, Lidija
Pavlović, Vladimir B.
Führer, Hermann
Kalvoda, Jaroslav
Mihailović, Milhailo Lj.
Article (Published version)
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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.
Keywords:
Macrocyclic Ring / Disecosteroids / 5,10:8,9‐Disecosteroids ( = Steroklastanes)
Source:
Helvetica Chimica Acta, 1992, 75, 1, 203-209
Publisher:
  • Weinheim : Wiley-VCH Verlag GmbH & Co.

DOI: 10.1002/hlca.19920750118

ISSN: 0018-019X

Scopus: 2-s2.0-0026505397
[ Google Scholar ]
6
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/4743
Collections
  • Radovi istraživača / Researchers' publications
Institution/Community
IHTM
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 . .

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