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Journal of Lipid Research, Vol 26, 874-881, Copyright © 1985 by Lipid Research, Inc.

ARTICLES

Potential bile acid metabolites. 9. 3,12-Dihydroxy- and 12 beta-hydroxy- 5 alpha-cholanoic acids

T Iida, T Tamura, T Matsumoto and FC Chang

Syntheses of the heretofore unreported 3 alpha, 12 beta-, 3 beta, 12 beta-dihydroxy-, and 12 beta-hydroxy-5 alpha-cholanic acids of the 5 alpha-series, their methyl esters, and some related derivatives are described. In addition, allodeoxycholic (3 alpha, 12 alpha-dihydroxy) acid was prepared by a new route. The principal reactions involved were the stereoselective reduction of C-12 ketones with an amino-borane reagent and of a C-3 ketone with K-Selectride, and inversion of a 3 beta-tosylate derivative with N,N-dimethylformamide.
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