Conversion of cholic acid to methyl 3alpha-carbethoxy-12alpha-acetoxy-6-oxo-5beta-chol-7-en-24-oate

Steroids. 2003 Mar;68(3):253-6. doi: 10.1016/s0039-128x(02)00182-4.

Abstract

A new and efficient method for preparation of a 7-en-6-one derivative of cholic acid is described. Acetylation of the known methyl 3alpha-carbethoxy-12alpha-hydroxy-7-oxo-5beta-cholan-24-oate (3) at 12 position and reduction of its 7-oxo group yield the 12alpha-acetoxy-7alpha-hydroxy derivative 5. Dehydration of the 7alpha-hydroxy group in 5 followed by allylic oxidation provide methyl 3alpha-carbethoxy-12alpha-acetoxy-6-oxo-5beta-chol-7-en-24-oate (7) in good yield.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry, Organic / methods
  • Cholic Acid / chemistry
  • Cholic Acid / metabolism*
  • Cholic Acids / chemistry
  • Cholic Acids / metabolism*
  • Spectrum Analysis
  • Stereoisomerism
  • X-Ray Diffraction

Substances

  • Cholic Acids
  • methyl 3-carbethoxy-12-acetoxy-6-oxochol-7-en-24-oate
  • Cholic Acid