Front side neighbouring group participation in the 16-hydroxymethylandrost-5-ene-3, 17-diol series

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4 Citations (Scopus)

Abstract

The cis isomers of 16-hydroxymethylandrost-5-ene-3β, 17-diol (1a and 8a) transform into 16-bromomethylandrost-5-ene-3β, 17 diacetate (5 and 12) on treatment with hydrogen bromide and acetic acid. The process is accompanied by the formation of some tri-acetate (1d and 8d) and rearranged products (6 and 13). The trans isomers (15a and 16a) yield, under similar experimental conditions, only triacetates (15b and 16b).

Original languageEnglish
Pages (from-to)2729-2732
Number of pages4
JournalTetrahedron
Volume38
Issue number17
DOIs
Publication statusPublished - 1982

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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