Potential Bile Acid Metabolites. XXI. A New Synthesis of Allochenodeoxycholic and Allocholic Acids1)

Takashi Iida, Shinji Nishida, Frederic C. Chang, Toshifumi Niwa, Junichi Goto, Toshio Nambara

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

Abstract

A new method for the preparation of allochenodeoxycholic and allocholic acids is described. The key steps in the synthesis are 1) simultaneous oxidation-dehydrogenation reaction of 3a-hydroxy 5β-bile acid formyl esters with iodoxybenzene catalyzed by benzeneseleninic anhydride, 2) reductive allomerization at C-5 of the 1,4-dien-3-oxo hydroxy acids with lithium/liq. ammonia, and 3) subsequent reduction of the resulting 3-oxo 5α-compounds with K-Selectride.

Original languageEnglish
Pages (from-to)763-765
Number of pages3
JournalChemical and Pharmaceutical Bulletin
Volume41
Issue number4
DOIs
Publication statusPublished - 1993

Keywords

  • 3α,7α,12α-trihydroxy-5α-cholanoic acid
  • 3α,7α-dihydroxy-5α-cholanoic acid
  • bile acid

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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