Synthesis of ester-linked lithocholic acid dimers

Alan Turner, L. Nahar

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

Four lithocholic acid dimers were synthesised via esterification. The ester-linked dimer, 3-oxo-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta), was obtained by condensation of methyl lithocholate with 3-oxo-5beta-cholan-24-oic acid. Borohydride reduction of this ester-linked dimer gave 3alpha-hydroxy-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta), which was acetylated to 3alpha-acetoxy-5beta-cholan-24-oic acid (cholan-24-oic acid methyl ester)-3-yl ester, (3alpha,5beta). Reaction of methyl lithocholate with oxalyl chloride yielded the oxalate dimer, bis(5beta-cholan-24-oic acid methyl ester)-3alpha-yl oxalate. (C) 2003 Elsevier Inc. All rights reserved.

Original languageEnglish
Pages (from-to)1157-1161
Number of pages4
JournalSteroids
Volume68
DOIs
Publication statusPublished - 2003

Keywords

  • lithocholic acid
  • steroid dimers
  • esterification
  • hydrolysis
  • C-13 NMR
  • BILE-ACIDS
  • STEROIDS
  • DERIVATIVES
  • BINDING
  • BIS

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