Progress toward the Total Synthesis of Goniodomin A: Stereocontrolled, Convergent Synthesis of the C12-C36 Fragment

Haruhiko Fuwa, Seiji Matsukida, Taro Miyoshi, Yuki Kawashima, Tomoyuki Saito, Makoto Sasaki

    Research output: Contribution to journalArticlepeer-review

    12 Citations (Scopus)

    Abstract

    Goniodomin A is a marine polyether macrolide natural product isolated from the dinoflagellate Alexandrium hiranoi. In this paper, we report stereocontrolled, convergent synthesis of a fully functionalized C12-C36 fragment of goniodomin A. The synthesis of the C12-C25 vinylstannane involved a Wittig reaction and a reductive cycloetherification for the construction of the dihydropyran ring. The C26-C36 thioester was synthesized via a Nozaki-Hiyama-Kishi reaction of an aldehyde and an iodoalkyne, the former of which was easily prepared from (R)-malic acid as a chiral source by taking advantage of substrate-controlled diastereoselective reactions. Finally, a palladium-catalyzed coupling of the C12-C25 vinylstannane and the C26-C36 thioester completed the synthesis of the target compound.

    Original languageEnglish
    Pages (from-to)2213-2227
    Number of pages15
    JournalJournal of Organic Chemistry
    Volume81
    Issue number6
    DOIs
    Publication statusPublished - 2016 Mar 18

    ASJC Scopus subject areas

    • Organic Chemistry

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