Synthetic studies on a marine polyether toxin, gambierol: Stereoselective synthesis of the EFGH ring system via B-alkyl Suzuki coupling

Haruhiko Fuwa, Makoto Sasaki, Kazuo Tachibana

    Research output: Contribution to journalArticle

    77 Citations (Scopus)

    Abstract

    A synthetic route to the EFGH ring system (3) of gambierol (1), a marine polyether toxin isolated from the dinoflagellate Gambierdiscus toxicus, has been developed. The present synthesis features convergent coupling of the F and H rings followed by ring-closure of the G ring based on the B-alkyl Suzuki reaction of lactone-derived enol phosphates. An angular methyl group at C23 was stereoselectively introduced by treatment of sulfone 32 with trimethylaluminum. Installation of a tertiary alcohol at C21 was accomplished through stereoselcetive dihydroxylation of exo-methylene 36 followed by selective formation of the primary p-toluensulfonate and treatment of the resultant monotosylate 40 with lithium aluminum hydride. Finally, formation of the E ring as a lactone form completed the synthesis of 3.

    Original languageEnglish
    Pages (from-to)3019-3033
    Number of pages15
    JournalTetrahedron
    Volume57
    Issue number15
    DOIs
    Publication statusPublished - 2001 Apr 9

    Keywords

    • Marine metabolites
    • Polyethers
    • Suzuki reactions
    • Toxins

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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