The structure of isobarbatene, the stable tricyclic end-point of the bazzanene-barbatene sesquiterpenes

Niels H. Anderson, Chia Li W Tseng, Ana L Moore, Yoshimoto Ohta

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15 Citations (Scopus)

Abstract

The barbatenes (e.g. 3) and a number of other sesquiterpenes afford a novel rearrangement product on treatment with CF3CO2H. This substance, designated isobarbatene, is shown to have structure 6, the result of a bicyclo-[3.2.1]→[2.2.2]→[3.2.1] rearrangement followed by an exo Me shift and deprotonation. The structure assignment is based on spectral and chiroptical data for olefin 6 and its degradation products 8,9 and 10.

Original languageEnglish
Pages (from-to)47-52
Number of pages6
JournalTetrahedron
Volume34
Issue number1
DOIs
Publication statusPublished - 1978

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ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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