Total Syntheses of Stoloniferol B and Penicitol A, and Structural Revision of Fusaraisochromanone

Tatsuki Ohashi, Seijiro Hosokawa

    研究成果: Article

    8 引用 (Scopus)

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    The first total synthesis of stoloniferol B and penicitol A has been achieved. Stoloniferol B, which is the common structure of citrinin derivatives, has been constructed by a sequential elaboration that includes a stereoselective vinylogous Mukaiyama aldol reaction, a thermal esterification with methyl acetoacetate, an intramolecular Michael reaction, and a vinylogous Dieckmann cyclization. The enantiomer of the proposed structure of fusaraisochromanone and (S)-7-hydroxy-3-((R)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one (the enantiomer of a natural stoloniferol derivative) also have been synthesized. The synthesis revised the structure of fusaraisochromanone to (S)-7-hydroxy-3-((R)-1-hydroxyethyl)-5-methoxy-3,4-dimethylisobenzofuran-1(3H)-one.

    元の言語English
    ページ(範囲)3021-3024
    ページ数4
    ジャーナルOrganic Letters
    20
    発行部数10
    DOI
    出版物ステータスPublished - 2018 5 18

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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