Potential bile acid metabolites. 19. The epimeric 3α,6,7β-trihydroxy-and 3α,6,7β,12α-tetrahydroxy-5α-cholanoic acids

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

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Syntheses by a new procedure of the known 3α,6α,7β- and 3α,6β,7β-trihydroxy-5α-cholanoic acids, and of the once-reported analog 3α,6α,7β,12α-, as well as the new 3α,6β,7β,12α-tetrahydroxy-5α-cholanoic acids, are described. Key intermediates of the syntheses are the 6-oxo-7β-ols of the respective 5α-cholanoic acids (and their methyl esters) prepared by allomerization at C-5 of appropriate 6-bromo-7-oxo derivatives of the corresponding 5β-acids. Successful reduction of the 6,7-ketols to the desired products depended on the proper choice of reagents, either Zn(BH4)2 or Li/NH3/MeOH. (Steroids 58:148-152, 1993).

Original languageEnglish
Pages (from-to)148-152
Number of pages5
JournalSteroids
Volume58
Issue number4
DOIs
Publication statusPublished - 1993 Apr

Keywords

  • 3α,6α,7β,12α-tetrahydroxy-5α-cholanoic acid
  • 3α,6α,7β-trihydroxy-5α-cholanoic acid
  • 3α,6β,7β,12α-tetrahydroxy-5α-cholanoic acid
  • 3α,6β,7β-trihydroxy-5α-cholanoic acid
  • allo bile acids
  • steroids

ASJC Scopus subject areas

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

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