Synthesis of a novel sesquiterpene isolated from the pheromone gland of a stink bug, Tynacantha marginata Dallas

Shigefumi Kuwahara, Shiharu Hamade, Walter Soares Leal, Jiro Ishikawa, Osamu Kodama

    Research output: Contribution to journalArticlepeer-review

    14 Citations (Scopus)

    Abstract

    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. (C) 2000 Elsevier Science Ltd.

    Original languageEnglish
    Pages (from-to)8111-8117
    Number of pages7
    JournalTetrahedron
    Volume56
    Issue number41
    DOIs
    Publication statusPublished - 2000 Oct 6

    Keywords

    • Cyclisation
    • Michael reactions
    • Pheromone
    • Terpenes and terpenoids

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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