A convenient synthesis of dinorbile acids: oxidative hydrolysis of norbile acid nitriles

Steroids. 1999 Nov;64(11):780-4. doi: 10.1016/s0039-128x(99)00064-1.

Abstract

We report a convenient method for the synthesis of dinorbile acids (23,24-dinor-5beta-cholan-22-oic acids, pregnane-20-carboxylic acids) in fair to good yields from norbile acid nitriles in one step by oxidative hydrolysis with oxygen in the presence of potassium-t-butoxide. The method results in stepwise overall removal of two carbon atoms in bile acid side chains in two steps. Dinorbile acids corresponding to several common bile acids have been prepared and their structures confirmed by spectroscopic methods. This simple method for synthesis of dinorbile acids may facilitate their study metabolically.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Bile Acids and Salts / chemical synthesis*
  • Carboxylic Acids / chemical synthesis*
  • Chromatography, Gas
  • Hydrolysis
  • Magnetic Resonance Spectroscopy
  • Oxidation-Reduction

Substances

  • Bile Acids and Salts
  • Carboxylic Acids