Journal of Lipid Research (Jul 1985)

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

  • T Iida,
  • T Tamura,
  • T Matsumoto,
  • F C Chang

Journal volume & issue
Vol. 26, no. 7
pp. 874 – 881

Abstract

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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.