Synthesis of bile acid analogs: 7-alkylated chenodeoxycholic acids.
This paper describes a method for the preparation of 7-alkylated chenodeoxycholic acids from 3 alpha-hydroxy-7-oxo-5 beta-cholanoic acid. The synthetic procedure is based upon a Grignard reaction between the keto bile acid and an alkyl magnesium halide. Under the conditions employed, the introduction of alkyl groups is highly stereoselective. Only 7 beta-alkylated epimers are obtained. The overall yield is several-fold higher than that obtained by the previous method, which involved the preparation of an oxazoline intermediate.
Institute of Pharmaceutical Sciences, Hiroshima University School of Medicine, Japan.
M
M
Une
K
K
Yamanaga
E H
EH
Mosbach
S
S
Kuroki
T
T
Hoshita
D001647:Bile Acids and Salts / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D003840:Deoxycholic Acid / Q000031:analogs & derivatives*; D013058:Mass Spectrometry; D014580:Ursodeoxycholic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D001647:Bile Acids and Salts; D003840:Deoxycholic Acid; C060839:3,7-dihydroxy-7-ethylcholanoic acid; C060838:3,7-dihydroxy-7-n-propylcholanoic acid; D014580:Ursodeoxycholic Acid; C041636:3,7-dihydroxy-7-methylcholanoic acid