A VERSATILE AND STRAIGHTFORWARD APPROACH TO THE 21-OXIDATION OF BETA-SUBSTITUTED AND ALPHA,BETA-UNSATURATED 20-OXOSTEROIDS

Authors
MORENO MJSM DACOSTA SP MARTINS RMLM MELO MLSE NEVES ASC
Citation
Mjsm. Moreno et al., A VERSATILE AND STRAIGHTFORWARD APPROACH TO THE 21-OXIDATION OF BETA-SUBSTITUTED AND ALPHA,BETA-UNSATURATED 20-OXOSTEROIDS, Tetrahedron, 54(45), 1998, pp. 13877-13886
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
45
Year of publication
1998
Pages
13877 - 13886
Database
ISI
SICI code
0040-4020(1998)54:45<13877:AVASAT>2.0.ZU;2-X
Abstract
21-Hydroxylation and acetoxylation of 20-oxosteroids, either alpha,bet a-unsaturated or beta- substituted, were successfully achieved through oxidation of the corresponding silyl enol ethers with m-CPBA followed by smooth hydrolytic cleavage of the 21-alkylsilyloxy derivatives. Th ese conditions, which have not been previously used to synthesize such compounds, allow a high degree of regio and chemoselectivity and are specially useful for the chemical synthesis of 16 alpha,21-dihydroxy-2 0-oxosteroids. (C) 1998 Elsevier Science Ltd. All rights reserved.