A convenient synthesis of dinorbile acids: Oxidative hydrolysis of norbileacid nitriles

We report a convenient method for the synthesis of dinorbile acids (23,24-d inor-5 beta-cholan-22-oic acids, pregnane-20-carboxylic acids) in fair to g ood yields from norbile acid nitriles in one step by oxidative hydrolysis w ith oxygen in the presence of potassium-t-butoxide. The method results in s tepwise overall removal of two carbon atoms in bile acid side chains in two steps. Dinorbile acids corresponding to several common bile acids have bee n prepared and their structures confirmed by spectroscopic methods. This si mple method for synthesis of dinorbile acids may facilitate their study met abolically. (C) 1999 Elsevier Science Inc. All rights reserved.