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  • Title: Potential bile acid metabolites. 14. Hyocholic and muricholic acid stereoisomers.
    Author: Iida T, Momose T, Tamura T, Matsumoto T, Chang FC, Goto J, Nambara T.
    Journal: J Lipid Res; 1989 Aug; 30(8):1267-79. PubMed ID: 2769078.
    Abstract:
    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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