Alternative synthesis of (24S)-homoethylcastasterone from stigmasterol

Authors
Centurion, OMT Galagovsky, LR
Citation
Omt. Centurion et Lr. Galagovsky, Alternative synthesis of (24S)-homoethylcastasterone from stigmasterol, AN AS QUIM, 86(3-6), 1998, pp. 104-109
Citations number
30
Categorie Soggetti
Chemistry
Journal title
ANALES DE LA ASOCIACION QUIMICA ARGENTINA
ISSN journal
03650375 → ACNP
Volume
86
Issue
3-6
Year of publication
1998
Pages
104 - 109
Database
ISI
SICI code
0365-0375(199805/12)86:3-6<104:ASO(FS>2.0.ZU;2-U
Abstract
24(S)-Homoethylcastasterone belongs to the group of natural products named brassinosteroids. This work reports its synthesis from stigmasterol through a new pathway which involves a reductive opening of a 5 beta,6 beta-steroi dal epoxide derivative. Key intermediate compound 4a also allows to develop pathways for the synthesis of highly active C-3 natural oxygenated brassin osteroids.