Enantioselective total syntheses of cyathane diterpenoids

    研究成果: Article査読

    24 被引用数 (Scopus)

    抄録

    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.

    本文言語English
    ページ(範囲)641-662
    ページ数22
    ジャーナルChemical record (New York, N.Y.)
    14
    4
    DOI
    出版ステータスPublished - 2014 8月 1

    ASJC Scopus subject areas

    • 化学 (全般)
    • 生化学
    • 化学工学(全般)
    • 生化学、医学
    • 材料化学

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