Contemporary strategies for the synthesis of Tetrahydropyran derivatives: Application to total synthesis of neopeltolide, a marine macrolide natural product

Haruhiko Fuwa

    Research output: Contribution to journalArticle

    20 Citations (Scopus)

    Abstract

    Tetrahydropyrans are structural motifs that are abundantly present in a range of biologically important marine natural products. As such, significant efforts have been paid to the development of efficient and versatile methods for the synthesis of tetrahydropyran derivatives. Neopeltolide, a potent antiproliferative marine natural product, has been an attractive target compound for synthetic chemists because of its complex structure comprised of a 14-membered macrolactone embedded with a tetrahydropyran ring, and twenty total and formal syntheses of this natural product have been reported so far. This review summarizes the total and formal syntheses of neopeltolide and its analogues, highlighting the synthetic strategies exploited for constructing the tetrahydropyran ring.

    Original languageEnglish
    Article number65
    JournalMarine Drugs
    Volume14
    Issue number4
    DOIs
    Publication statusPublished - 2016 Apr

    Keywords

    • Hetero-Diels-Alder cycloadditions
    • Oxa-Michael reactions
    • Oxocarbenium ions
    • Oxymercurations
    • Palladium-catalyzed alkoxycarbonylations
    • Radical cyclizations
    • Ring-closing metathesis
    • Synthetic methods
    • Tetrahydropyrans

    ASJC Scopus subject areas

    • Drug Discovery

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