Enantioselective total syntheses of cyathane diterpenoids

    Research output: Contribution to journalArticle

    18 Citations (Scopus)

    Abstract

    A Personal Account describing the enantioselective total syntheses of cyathane diterpenoids achieved in the Nakada group. A convergent approach to the cyathane scaffold, the [5-6-7] tricyclic carbon skeleton commonly found in cyathane diterpenoids, has been developed using the catalytic asymmetric intramolecular cyclopropanation (CAIMCP) and baker's yeast reduction. This approach has been successfully applied for the enantioselective total syntheses of (+)-allocyathin B2 , (-)-erinacine B, and (-)-erinacine E. The total synthesis of (-)-erinacine E has been achieved via the acyl group migratory intramolecular aldol reaction, which prevents the retro-aldol reaction and allows the construction of the strained structure. The highly efficient and stereoselective total syntheses of (-)-scabronines G, A, D, and (-)-episcabronine A have been achieved via the oxidative dearomatization/inverse electron demand Diels-Alder reaction cascade. Cascade reactions comprising three and five consecutive reactions were employed for the highly efficient total syntheses of (-)-scabronine A and (-)-episcabronine A, respectively.

    Original languageEnglish
    Pages (from-to)641-662
    Number of pages22
    JournalChemical record (New York, N.Y.)
    Volume14
    Issue number4
    DOIs
    Publication statusPublished - 2014 Aug 1

    Fingerprint

    Diterpenes
    Cycloaddition Reaction
    Skeleton
    Saccharomyces cerevisiae
    Carbon
    Electrons
    Scaffolds
    Yeast
    cyathane
    scabronine A
    3-hydroxybutanal
    erinacine E

    Keywords

    • asymmetric synthesis
    • cascade reactions
    • cyathanes
    • natural products
    • total synthesis

    ASJC Scopus subject areas

    • Chemistry(all)
    • Biochemistry
    • Chemical Engineering(all)
    • Biochemistry, medical
    • Materials Chemistry

    Cite this

    Enantioselective total syntheses of cyathane diterpenoids. / Nakada, Masahisa.

    In: Chemical record (New York, N.Y.), Vol. 14, No. 4, 01.08.2014, p. 641-662.

    Research output: Contribution to journalArticle

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