Total Synthesis of Polycavernosides A and B, Two Lethal Toxins from Red Alga

Kotaro Iwasaki, Satori Sasaki, Yusuke Kasai, Yuki Kawashima, Shohei Sasaki, Takanori Ito, Mari Yotsu-Yamashita, Makoto Sasaki

    Research output: Contribution to journalArticlepeer-review

    3 Citations (Scopus)

    Abstract

    Polycavernosides A and B are glycosidic macrolide natural products isolated as the toxins causing fatal human poisoning by the edible red alga Gracilaria edulis (Polycavernosa tsudai). Total synthesis of polycavernosides A and B has been achieved via a convergent approach. The synthesis of the macrolactone core structure is highlighted by the catalytic asymmetric syntheses of the two key fragments using hetero-Diels-Alder reaction and Kiyooka aldol reaction as the key steps, their union through Suzuki-Miyaura coupling, and Keck macrolactonization. Finally, glycosylation with the l-fucosyl-d-xylose unit and construction of the polyene side chain through Stille coupling completed the total synthesis of polycavernosides A and B.

    Original languageEnglish
    Pages (from-to)13204-13219
    Number of pages16
    JournalJournal of Organic Chemistry
    Volume82
    Issue number24
    DOIs
    Publication statusPublished - 2017 Dec 15

    ASJC Scopus subject areas

    • Organic Chemistry

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