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Steroids. 1993 Feb;58(2):52-8.

An efficient synthesis of 4 beta- and 6 alpha-hydroxylated bile acids.

Author information

1
Faculty of Pharmaceutical Sciences, Higashi-Nippon-Gakuen University, Hokkaido, Japan.

Abstract

An efficient method for the preparation of 4 beta- and 6 alpha-hydroxylated bile acids has been developed. It involved a highly stereoselective acetoxylation at the 4 beta and 6 alpha positions of 3- and 7-oxo bile acids, respectively, with lead tetraacetate in the presence of boron trifluoride etherate in acetic acid. Reduction of the resulting alpha-acetoxy ketones with sodium borohydride or tert-butylamine borane complex, and alkaline hydrolysis, provided the desired bile acids in good yields.

PMID:
8484184
DOI:
10.1016/0039-128x(93)90052-o
[Indexed for MEDLINE]

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