A general strategy for the convergent synthesis of fused polycyclic ethers via B-alkyl Suzuki coupling: Synthesis of the ABCD ring fragment of ciguatoxins

Makoto Sasaki, Makoto Ishikawa, Haruhiko Fuwa, Kazuo Tachibana

    Research output: Contribution to journalArticle

    86 Citations (Scopus)

    Abstract

    A new method for convergent coupling of fused polycyclic ethers has been developed, which relies on B-alkyl Suzuki crosscoupling of lactone-derived enol triflates or phosphates. The strategy was successfully applied to a convergent synthesis of the ABCD ring fragment 4 of ciguatoxins, the causative toxin for ciguatera fish poisoning. The synthetic route includes a convergent union of the B and D rings (18 and 29c, respectively) by the B-alkyl Suzuki coupling, introduction of a double bond into the D ring followed by reductive closure of the tetrahydropyran C ring to afford the BCD ring system 51, and, finally, ring-closing metathesis reaction to construct the oxepene A ring.

    Original languageEnglish
    Pages (from-to)1889-1911
    Number of pages23
    JournalTetrahedron
    Volume58
    Issue number10
    DOIs
    Publication statusPublished - 2002 Mar 4

    Keywords

    • Marine metabolites
    • Polyethers
    • Ring-closing metathesis
    • Suzuki reactions
    • Toxins

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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