Neighboring group participation. Part 14. The preparation of the four stereoisomers of 16-hydroxymethyl-5α-androstane-3β,17-diol

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Abstract

16α-Hydroxymethyl-5α-androstane-3β,17β-diol and 16β-hydroxymethyl-5α-androstane-3β,17β-diol, were obtained from reduction of 16-acetoxymethylene-5α-androstan-17-one. The corresponding 16α,17α- and 16β,17α-hydroxymethyl isomers were obtained by neighboring group participation of the 16- and 17-acetates, respectively. The reactions involving carbocation formation also led to ring D rearrangement products.

Original languageEnglish
Pages (from-to)623-635
Number of pages13
JournalSteroids
Volume66
Issue number8
DOIs
Publication statusPublished - Jul 12 2001

Keywords

  • 16-Hydroxymethyl-5α-androstane-3β,17-diol
  • Acetolysis
  • Neighboring group participation
  • Wagner-Meerwein rearrangement

ASJC Scopus subject areas

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

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