A convenient synthesis of dinorbile acids: oxidative hydrolysis of norbile acid nitriles.
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.
Batta
A K
AK
Department of Medicine, University of Medicine and Dentistry-New Jersey Medical School, Newark 07103, USA.
Datta
S C
SC
Tint
G S
GS
Alberts
D S
DS
Earnest
D L
DL
Salen
G
G
D001647:Bile Acids and Salts / Q000138:chemical synthesis*; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D002849:Chromatography, Gas; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction
D001647:Bile Acids and Salts; D002264:Carboxylic Acids