title: Potential bile acid metabolites. 9. 3,12-Dihydroxy- and 12 beta-hydroxy-5 alpha-cholanoic acids.
abstract: 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.
mesh_terms: D001647:Bile Acids and Salts / Q000378:metabolism; D055598:Chemical Phenomena; D002621:Chemistry; D003840:Deoxycholic Acid / Q000138:chemical synthesis*; D008095:Lithocholic Acid / Q000031:analogs & derivatives / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D001647:Bile Acids and Salts; D003840:Deoxycholic Acid; D008095:Lithocholic Acid