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Journal of Chemical Ecology

, Volume 17, Issue 3, pp 663–685 | Cite as

Identification and preparation of antiinsectan dienols fromDipterocarpus kerrii tree resins

  • David P. Richardson
  • Adam C. Messer
  • Blair A. Newton
  • Neal I. Lindeman
Article

Abstract

Originally isolated fromDipterocarpus kerrii, the two previously uncharacterized sesquiterpenes,1 and20, were synthesized from α-gurjunene. A novel process involvingm-chloroperoxybenzoic acid oxidation ofα-gurjunene produced20 in one step. Spectroscopic studies determined that the diene moiety in20 is nonconjugated and also found the C-4 tertiary alcohol center to have theα-configuration, while the other stereocenters have configurations matching the corresponding centers inα-gurjunene. Bioassays with termites demonstrated that20 was more toxic than1, resulting in a 50% mortality in seven days when offered toNeotermes ?dalbergiae on filter papers. The chemicals appear to result from biotransformation ofα-gurjunene. In view of its similarity to the known sesquiterpeneγ-gurjunene, we suggest that20 be referred to asγ-gurjunenol.

Key words

Dipterocarpus kerrii sesquiterpenes chemical synthesis dienol tropical biology termiticide Neotermes α-gurjunene γ-gurjunene γ-gurjunenol bioassay stereochemistry 

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Copyright information

© Plenum Publishing Corporation 1991

Authors and Affiliations

  • David P. Richardson
    • 1
  • Adam C. Messer
    • 2
  • Blair A. Newton
    • 1
  • Neal I. Lindeman
    • 1
  1. 1.Department of ChemistryWilliams CollegeWilliamstown
  2. 2.School of Food and Nutritional ScienceUniversity of ShizuokaShizuokaJapan

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