Synthesis and biological activity of the QRS ring system of maitotoxin

Hisaaki Onoue, Tomomi Baba, Keiichi Konoki, Kohei Torikai, Makoto Ebine, Tohru Oishi

    Research output: Contribution to journalArticlepeer-review

    12 Citations (Scopus)

    Abstract

    Maitotoxin (MTX) is a ladder-shaped polyether produced by an epiphytic dinoflagellate. As a part of our structure-activity relationship studies using synthetic partial structures of MTX, the QRS ring comprising a 6/6/7 tricyclic system was synthesized through stereoselective construction of five contiguous stereogenic centers on the Q ring via i) coupling of a Weinreb amide and a furyllithium, followed by ii) Noyori asymmetric transfer hydrogenation, iii) the Achmatowicz reaction, iv) chemoselective methylation of a methyl acetal in the presence of a carbonyl group by treatment with Me2Zn/BF3·OEt2, v) highly diastereoselective dihydroxylation, and vi) ring expansion of a six-membered to a seven-membered ring ketone. The synthetic specimen inhibited MTX-induced Ca2+influx with an IC50 value of 44 μM.

    Original languageEnglish
    Pages (from-to)1904-1906
    Number of pages3
    JournalChemistry Letters
    Volume43
    Issue number12
    DOIs
    Publication statusPublished - 2014

    ASJC Scopus subject areas

    • Chemistry(all)

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