An efficient synthesis of 4 beta- and 6 alpha-hydroxylated bile acids

Steroids. 1993 Feb;58(2):52-8. doi: 10.1016/0039-128x(93)90052-o.

Abstract

An efficient method for the preparation of 4 beta- and 6 alpha-hydroxylated bile acids has been developed. It involved a highly stereoselective acetoxylation at the 4 beta and 6 alpha positions of 3- and 7-oxo bile acids, respectively, with lead tetraacetate in the presence of boron trifluoride etherate in acetic acid. Reduction of the resulting alpha-acetoxy ketones with sodium borohydride or tert-butylamine borane complex, and alkaline hydrolysis, provided the desired bile acids in good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates
  • Acetic Acid
  • Bile Acids and Salts / chemical synthesis*
  • Boranes
  • Borohydrides
  • Cholic Acids / chemistry
  • Humans
  • Hydroxylation
  • Ketones / chemistry
  • Molecular Structure
  • Organometallic Compounds
  • Oxidation-Reduction

Substances

  • Acetates
  • Bile Acids and Salts
  • Boranes
  • Borohydrides
  • Cholic Acids
  • Ketones
  • Organometallic Compounds
  • boron trifluoride
  • sodium borohydride
  • lead tetraacetate
  • cholanic acid
  • Acetic Acid