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- Title
Opening of the Macrocyclic Ring in 5,10:8,9-Disecosteroids ( = Steroklastanes).
- Authors
Lorenc, Ljubinka; Bondarenko-Gheorghiu, Lidija; Pavlović, Vladimir; Fuhrer, Hermann; Kalvoda, Jaroslav; Mihailović, Mihailo Lj.
- Abstract
Catalytic hydrogenation of the Δ3-unsaturated (9 R,10 R)- and (9 S,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 (9 R,10 R)- and (9 S,10 S)-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 (9 R,10 R)- and (9 S,10 S)-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.
- Publication
Helvetica Chimica Acta, 1992, Vol 75, Issue 1, p203
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19920750118