Synthesis of 3 α,7 α,14 α-trihydroxy-5 β-cholan-24-oic acid: A potential primary bile acid in vertebrates

Genta Kakiyama, Takashi Iida, Takaaki Goto, Nariyasu Mano, Junichi Goto, Toshio Nambara

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

A method for the synthesis of 3 α,7 α,14 α-trihydroxy-5 β-cholan-24-oic acid which is a possible candidate of bile acid metabolite in vertebrates was developed. The principal reactions involved were 1) stereoselective remote-hydroxylation of methyl ursodeoxycholate diacetate with dimethyldioxirane, 2) site-selective protection at C-3 by tert- butyldimethylsilylation of the resulting 3 α,7 α,14 α-trihydroxy ester, 3) oxidation of the diol with pyridinium dichromate adsorbed on activated alumina, 4) stereoselective reduction of the 7-ketone with zinc borohydride, and 5) cleavage of the protecting group at C-3 with p-toluenesulfonic acid. A facile elimination of the 14 α-hydroxy group under an acidic or neutral condition is also described. The synthetic reference compound is now available for comparison with unidentified biliary bile acids detected in vertebrate bile.

Original languageEnglish
Pages (from-to)371-374
Number of pages4
JournalChemical and Pharmaceutical Bulletin
Volume52
Issue number3
DOIs
Publication statusPublished - 2004 Mar

Keywords

  • 3 α,7 α,14 α-trihydroxy-5 β-cholan-24-oic acid
  • Dimethyldioxirane
  • Remote-hydroxylation

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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