Preparation of novel synthons, uniquely functionalized tetrahydrofuran and tetrahydropyran derivatives

Masahisa Nakada, Masashi Takano, Yukitaka Iwata

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    3 Citations (Scopus)

    Abstract

    The dianion of the acetoacetic ester reacts with epibromohydrin derivatives to afford a mixture of (Z)-2-alkoxycarbonylmethylidenetetrahydrofuran derivative and (E)-2-alkoxycarbonylmethylidenetetrahydropyran derivative. The selective formation of the tetrahydrofuran derivative is achieved by the use of LiCIO4 as the additive. The preparation of the optically active tetrahydrofuran derivatives and tetrahydropyran derivatives is also examined, and the optical purity and absolute configuration of the products is elucidated.

    Original languageEnglish
    Pages (from-to)1581-1585
    Number of pages5
    JournalChemical and Pharmaceutical Bulletin
    Volume48
    Issue number10
    Publication statusPublished - 2000

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    Keywords

    • Acetoacetic ester
    • Dianion
    • Epibromohydrin
    • Epoxide
    • Tetrahydrofuran
    • Tetrahydropyran

    ASJC Scopus subject areas

    • Drug Discovery
    • Organic Chemistry
    • Chemistry(all)
    • Pharmacology

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