Biosynthesis-inspired intramolecular oxa-conjugate cyclization of α,β-unsaturated thioesters: Stereoselective synthesis of 2,6-cis-substituted tetrahydropyrans

Haruhiko Fuwa, Kenkichi Noto, Makoto Sasaki

    Research output: Contribution to journalArticle

    26 Citations (Scopus)

    Abstract

    Intramolecular oxa-conjugate cyclization of α,β-unsaturated thioesters under Brønsted acid catalysis, inspired by biosynthesis of polyketide natural products, provides a variety of 2,6-cis-substituted tetrahydropyran derivatives with excellent diastereoselectivities. An added bonus of this methodology is that the product tetrahydropyrans could be readily elaborated to various derivatives by exploiting the unique reactivity of the thioester group.

    Original languageEnglish
    Pages (from-to)1820-1823
    Number of pages4
    JournalOrganic letters
    Volume13
    Issue number7
    DOIs
    Publication statusPublished - 2011 Apr 1

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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