Total synthesis of (-)-brevenal: A streamlined strategy for practical synthesis of polycyclic ethers

Makoto Ebine, Haruhiko Fuwa, Makoto Sasaki

    Research output: Contribution to journalArticlepeer-review

    13 Citations (Scopus)

    Abstract

    We describe a streamlined strategy for the practical synthesis of trans-fused polycyclic ethers and its application to a concise total synthesis of (-)-brevenal, a new pentacyclic polyether natural product with intriguing biological activities. The B-, D-, and E-rings were constructed by TEMPO/PhI(OAc)2-mediated oxidative lactonization of the corresponding 1,6-diols, with minimal need for manipulation of oxygen functionalities. The B- and E-ring lactones were appropriately functionalized by Suzuki-Miyaura coupling of lactone-derived enol phosphates and subsequent stereoselective hydroboration. The A-ring was formed by our mixed thioacetalization methodology. The AB- and DE-ring fragments were assembled through Suzuki-Miyaura coupling, and the C-ring was forged in the same manner as that for the A-ring. More than two grams of the pentacyclic polyether core of (-)-brevenal have been synthesized by the synthetic route developed in this study.

    Original languageEnglish
    Pages (from-to)13754-13761
    Number of pages8
    JournalChemistry - A European Journal
    Volume17
    Issue number49
    DOIs
    Publication statusPublished - 2011 Dec 2

    Keywords

    • cross-coupling
    • natural products
    • oxacycles
    • oxidation
    • polyethers

    ASJC Scopus subject areas

    • Catalysis
    • Organic Chemistry

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