OXYFUNCTIONALIZATION OF (5-BETA)-BILE ACIDS BY DIMETHYLDIOXIRANE - HYDROXYLATION AT C-5, C-14, AND C-17

Authors
CERRE C HOFMANN AF SCHTEINGART CD JIA WP MALTBY D
Citation
C. Cerre et al., OXYFUNCTIONALIZATION OF (5-BETA)-BILE ACIDS BY DIMETHYLDIOXIRANE - HYDROXYLATION AT C-5, C-14, AND C-17, Tetrahedron, 53(2), 1997, pp. 435-446
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
2
Year of publication
1997
Pages
435 - 446
Database
ISI
SICI code
0040-4020(1997)53:2<435:OO(ABD>2.0.ZU;2-V
Abstract
Dimethyldioxirane in chloroform Solution is an efficient reagent for t he tertiary hydroxylation of a series of methyl ester peracetate (5 be ta)-bile acid derivatives. 5 beta-Hydroxylation was observed in all ca ses, but the presence of a 7-acetyloxy substituent reduced reactivity of the 5 beta position allowing competitive 14 alpha- and 17 alpha-fun ctionalization subject to steric and electronic constraints. Copyright (C) 1996 Elsevier Science Ltd