Correction of the structure of a new sesquiterpene from Cistus creticus ssp. creticus

J Nat Prod. 2004 Dec;67(12):1996-2001. doi: 10.1021/np0498556.

Abstract

In an attempt to identify the structure of a sesquiterpene from Cistus creticus ssp. creticus proposed in the literature as 1,1,4a,6-tetramethyl-5-methylene-1,2,3,4,4alpha,5,8,8alpha-octahydronaphthalene, the synthesis of its cis isomer 2 was carried out in 11 steps and 9.5% yield. Comparison of the spectra of 2 and those reported earlier for the synthetic trans isomer 1 with the spectral profile of the isolated natural product indicated that the latter was not compatible with either 1 or 2. The correct structure was assigned, by detailed spectroscopic analysis of the natural product, as 6-isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (3).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cistus / chemistry*
  • Indicators and Reagents
  • Molecular Structure
  • Naphthalenes / chemistry*
  • Nuclear Magnetic Resonance, Biomolecular
  • Plants, Medicinal / chemistry*
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes / chemical synthesis
  • Sesquiterpenes / chemistry*
  • Stereoisomerism

Substances

  • 6-isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene
  • Indicators and Reagents
  • Naphthalenes
  • Polycyclic Sesquiterpenes
  • Sesquiterpenes
  • drimane