Oxyfunctionalization of (5β)-Bile Acids by Dimethyldioxirane: Hydroxylation at C-5, C-14, and C-17

Dimethyldioxirane in chloroform solution is an efficient reagent for the tertiary hydroxylation of a series of methyl ester peracetate (5β)-bile acid derivatives. 5β-Hydroxylation was observed in all cases, but the presence of a 7-acetyloxy substituent reduced reactivity of the 5β position allowing...

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Bibliographic Details
Published inTetrahedron Vol. 53; no. 2; pp. 435 - 446
Main Authors Cerrè, Carolina, Hofmann, Alan F., Schteingart, Claudio D., Jia, Weiping, Maltby, David
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 01.01.1997
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CHAIN
METHYL(TRIFLUOROMETHYL)DIOXIRANE
STEROIDS
DIOXIRANES
BOND INSERTION REACTION
TERTIARY
C-H BONDS
BILE-ACIDS
ASSIGNMENTS
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Summary:Dimethyldioxirane in chloroform solution is an efficient reagent for the tertiary hydroxylation of a series of methyl ester peracetate (5β)-bile acid derivatives. 5β-Hydroxylation was observed in all cases, but the presence of a 7-acetyloxy substituent reduced reactivity of the 5β position allowing competitive 14α- and 17α-functionalization subject to steric and electronic constraints. The presence of a 7-acetyloxy group in 5β-bile acid derivatives reduces the reactivity of DMDO in CHCl 3 toward the 5β position resulting in hydroxylation at C-14α and/or C-17α depending on steric factors.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(96)01062-9