Synthesis of a Novel Sesquiterpene Isolated from the Pheromone Gland of a Stink Bug, Tynacantha marginata Dallas

A novel sesquiterpene, isolated as the putative sex pheromone of a stink bug ( Tynacantha marginata Dallas) and proposed to have an unprecedented carbon framework, was synthesized as its racemate by using an intramolecular double Michael cyclization as the key step. Comparison of the spectral data o...

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Bibliographic Details
Published in:Tetrahedron 2000-10, Vol.56 (41), p.8111-8117
Main Authors: Kuwahara, Shigefumi, Hamade, Shiharu, Leal, Walter Soares, Ishikawa, Jiro, Kodama, Osamu
Format: Article
Language:English
Subjects:
cyclisation
Michael reactions
pheromone
terpenes and terpenoids
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Summary:A novel sesquiterpene, isolated as the putative sex pheromone of a stink bug ( Tynacantha marginata Dallas) and proposed to have an unprecedented carbon framework, was synthesized as its racemate by using an intramolecular double Michael cyclization as the key step. Comparison of the spectral data of the synthetic sample with those of the natural material confirmed the proposed structure.
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(00)00735-3