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Journal of Lipid Research, Vol 30, 1267-1279, Copyright © 1989 by Lipid Research, Inc.

ARTICLES

Potential bile acid metabolites. 14. Hyocholic and muricholic acid stereoisomers

T Iida, T Momose, T Tamura, T Matsumoto, FC Chang, J Goto and T Nambara
College of Engineering, Nihon University, Fukushima-ken, Japan.

The complete set of the eight theoretically possible stereoisomeric 3,6,7-trihydroxy-5 beta-cholanic acids, four of which are new, related to hyocholic and muricholic acids were prepared from chenodeoxycholic acid. The principal reactions used were 1) cis-dihydroxylation of delta 6-compounds with osmium tetroxide/N-methylmorpholine N-oxide; 2) trans- dihydroxylation of 6 alpha, 7 alpha-epoxy compounds with boron trifluoride etherate in N,N-dimethyl-formamide; 3) inversion of equatorial 3 alpha-hydroxylated compounds to the corresponding 3 beta- epimers with diethyl azodicarboxylate/triphenylphosphine/formic acid; and 4) stereoselective reduction of 7-keto derivatives with zinc borohydride (or sodium borohydride) and by metallic potassium/tert-amyl alcohol.
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