STEREOSPECIFIC SYNTHESIS OF STEROIDAL 20,16-GAMMA-CARBOLACTONES

Authors
BRUTTOMESSO AC DOLLER D GROS EG
Citation
Ac. Bruttomesso et al., STEREOSPECIFIC SYNTHESIS OF STEROIDAL 20,16-GAMMA-CARBOLACTONES, Synthetic communications, 28(21), 1998, pp. 4043-4057
Citations number
21
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthetic communications → ACNP
ISSN journal
00397911
Volume
28
Issue
21
Year of publication
1998
Pages
4043 - 4057
Database
ISI
SICI code
0039-7911(1998)28:21<4043:SSOS2>2.0.ZU;2-P
Abstract
Two strategies have been explored for the synthesis of steroidal 20,16 -gamma-carbolactones from the corresponding 17-ketoandrostane. A highl y efficient, stereospecific protocol has been developed for the P-orie nted cis-gamma-lactone, based on a Michael addition of cyanide to a co njugated ketone. A different approach, involving prior attachment of a 3-carbon side chain on C-17 of a 17-oxo-16 beta-acetoxy-androstane le d to the epimeric, alpha-oriented lactone.