Enantioselective total synthesis of enokipodins A-D, antimicrobial sesquiterpenes produced by the mushroom, Flammulina velutipes

Mana Saito, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    26 Citations (Scopus)

    Abstract

    The first enantioselective total synthesis of enokipodins A, B, C and D, highly oxidized α-cuparenone-type sesquiterpenoids possessing antimicrobial activity, was accomplished in 8-28% overall yields from methyl (2,5-dimethoxy-4-methylphenyl)acetate by applying Meyers' diastereoselective alkylation protocol for the construction of their C7-quaternary asymmetric center. The present synthesis confirmed the absolute configuration of the enokipodins, and also constitutes a formal enantioselective synthesis of (S)-1,4-cuparenediol and (S)-cuparene-1,4-quinone.

    Original languageEnglish
    Pages (from-to)374-381
    Number of pages8
    JournalBioscience, Biotechnology and Biochemistry
    Volume69
    Issue number2
    DOIs
    Publication statusPublished - 2005 Feb

    Keywords

    • Antibiotic
    • Cuparene
    • Enokipodin
    • Terpenoid

    ASJC Scopus subject areas

    • Biotechnology
    • Analytical Chemistry
    • Biochemistry
    • Applied Microbiology and Biotechnology
    • Molecular Biology
    • Organic Chemistry

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