Oxidative bromination of tricyclic sesquiterpenoids (1S,3S,5R,6S,9S)-5-hydroxy-6,10,10-trimethyl-tricyclo[7.2.0.0 1,6]udecan-2-one and clovane-2β,9α-diol with the HBr-DMSO system

M. S. Yusubov, Larisa Alexandrovna Drygunova, A. V. Tkachev

Research output: Contribution to journalArticle

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Abstract

Oxidation of tricyclic sesquiterpenoids of the caryophyllene type with the HBr-DMSO system afforded α,β-unsaturated a-bromoketones. Since tricyclic derivatives, unlike simple alicyclic ketones, cannot undergo aromatization, all intermediate oxidation products can be isolated, which provide evidence that oxidation proceeds according to the following scheme: ketone→α-bromoketone→α,α-dibromoketone→α, β-unsaturated α-bromoketone.

Original languageEnglish
Pages (from-to)1419-1422
Number of pages4
JournalRussian Chemical Bulletin
Volume50
Issue number8
DOIs
Publication statusPublished - 2001

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Keywords

  • Bromination
  • Caryophyllene
  • Dimethyl sulfoxide
  • Hydrobromic acid
  • Ketones
  • Oxidation
  • Tricyclic sesquiterpenoids

ASJC Scopus subject areas

  • Chemistry(all)

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