Enantioselective synthesis of hushinone, birkenol, and birkenal

Takafumi Hirokawa, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    7 Citations (Scopus)

    Abstract

    The first enantioselective synthesis of hushinone, a tricyclic norsesquiterpenoid with an unprecedented carbon framework identified from the essential oils of birch trees, was accomplished by using intramolecular halolactone alkylation as the key step. Two other bicyclic norsesquiterpenoids in the essential oils, birkenol and birkenal, which share the same carbon skeleton as hushinone, were also synthesized for the first time through eliminative lactone ring opening of hushinone. Comparison of the specific rotation data between the synthetic and natural products led to the confirmation of the absolute configuration of the natural products.

    Original languageEnglish
    Pages (from-to)2780-2782
    Number of pages3
    JournalEuropean Journal of Organic Chemistry
    Issue number14
    DOIs
    Publication statusPublished - 2013 May

    Keywords

    • Cyclization
    • Elimination
    • Natural products
    • Terpenoids
    • Total synthesis

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry
    • Organic Chemistry

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