Opening of the Macrocyclic Ring in 5,10:8,9‐Disecosteroids ( = Steroklastanes)
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1992
Authors
Lorenc, LjubinkaBondarenko-Gheorghiu, Lidija
Pavlović, Vladimir B.

Führer, Hermann
Kalvoda, Jaroslav
Mihailović, Milhailo Lj.
Article (Published version)

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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, 203-209Publisher:
- Weinheim : Wiley-VCH Verlag GmbH & Co.
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IHTMTY - 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 . .