Asymmetric total synthesis of (–)-rossinone A

Katsuya Saito, Kazuki Kurasawa, Chiaki Takino, Shigefumi Kuwahara, Masaru Enomoto

    Research output: Contribution to journalArticlepeer-review

    Abstract

    The asymmetric total synthesis of (–)-rossinone A, a meroterpene exhibiting a range of pharmacologically important biological activities, has been accomplished for the first time from geraniol by a concise eight-step sequence that involves the Horner–Wadsworth–Emmons reaction of an aldehyde derived from a geranylated hydroquinone intermediate with a chiral phosphonate prepared via the highly diastereoselective Davis oxidation of a known oxazolidinone derivative.

    Original languageEnglish
    Article number153456
    JournalTetrahedron Letters
    Volume84
    DOIs
    Publication statusPublished - 2021 Nov 9

    Keywords

    • Davis oxidation
    • Horner–Wadsworth–Emmons reaction
    • Meroterpene
    • Rossinone

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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