Studies toward the total synthesis of gambieric acids, potent antifungal polycyclic ethers: Convergent synthesis of a fully elaborated GHIJ-ring fragment

Koichi Tsubone, Keisuke Hashizume, Haruhiko Fuwa, Makoto Sasaki

    Research output: Contribution to journalArticlepeer-review

    15 Citations (Scopus)

    Abstract

    A stereocontrolled synthesis of a fully elaborated GHIJ-ring fragment of gambieric acids, which are potent antifungal polycyclic ether natural products, has been accomplished. The synthesis features convergent assembly of the tetracyclic polyether skeleton through aldol coupling/cyclodehydration/reductive etherification processes and stereoselective construction of the J-ring side chain by a CeCl3-promoted Julia-Kocienski olefination.

    Original languageEnglish
    Pages (from-to)6600-6615
    Number of pages16
    JournalTetrahedron
    Volume67
    Issue number35
    DOIs
    Publication statusPublished - 2011 Sep 2

    Keywords

    • Convergent synthesis
    • Gambieric acids
    • Julia-Kocienski olefination
    • Polycyclic ethers

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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