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

Ashok K. Batta, Subhash C. Datta, G. Stephen Tint, David S. Alberts, David L. Earnest, Gerald Salen

Research output: Contribution to journalArticle

4 Scopus citations

Abstract

We report a convenient method for the synthesis of dinorbile acids (23,24-dinor-5β-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.

Original languageEnglish (US)
Pages (from-to)780-784
Number of pages5
JournalSteroids
Volume64
Issue number11
DOIs
StatePublished - Nov 5 1999

Keywords

  • Bile acids
  • Dinorbile acids
  • Mass spectrometry
  • Norbile acids
  • Nuclear magnetic resonance
  • Synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

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