Potential bile acid metabolites. 14. Hyocholic and muricholic acid stereoisomers.
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.
College of Engineering, Nihon University, Fukushima-ken, Japan.
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Iida
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Momose
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Tamura
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Matsumoto
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Chang
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Goto
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Nambara
D001647:Bile Acids and Salts / Q000378:metabolism*; D002793:Cholic Acids / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D001647:Bile Acids and Salts; D002793:Cholic Acids; C004821:muricholic acid