A new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones via palladium-catalyzed coupling of thioesters

Haruhiko Fuwa, Kana Mizunuma, Seiji Matsukida, Makoto Sasaki

    Research output: Contribution to journalArticlepeer-review

    25 Citations (Scopus)

    Abstract

    In this paper, we describe a new strategy for the synthesis of substituted dihydropyrones and tetrahydropyrones. By exploiting palladium-catalyzed coupling of thioesters with terminal alkynes or alkenylboronic acids, a variety of β-hydroxy ynones or enones, respectively, could be prepared in an efficient manner under mild conditions. AgOTf-promoted intramolecular oxa-conjugate cyclization of β-hydroxy ynones provided 2,6-substituted dihydropyrones in excellent yields. On the other hand, acid-catalyzed cyclization of β-hydroxy enones caused racemization of the product 2,6-substituted tetrahydropyrones due to its reversible nature. Eventually, stereoselective hydrogenation of substituted dihydropyrones was found to be a solid and efficient approach for the synthesis of 2,6-cis-substituted tetrahydropyrone derivatives.

    Original languageEnglish
    Pages (from-to)4995-5010
    Number of pages16
    JournalTetrahedron
    Volume67
    Issue number27-28
    DOIs
    Publication statusPublished - 2011 Jul 8

    Keywords

    • Dihydropyrones
    • Intramolecular oxa-conjugate cyclization
    • Palladium-catalyzed coupling
    • Tetrahydropyrones
    • Thioesters

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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