Synthetic studies on antascomicin A: Construction of the C18-C34 fragment

Haruhiko Fuwa, Yumiko Okamura, Hideaki Natsugari

    Research output: Contribution to journalArticlepeer-review

    33 Citations (Scopus)

    Abstract

    Stereoselective synthesis of the C18-C34 fragment of antascomicin A is described. Construction of the C27-C34 carbocycle moiety was achieved via catalytic Ferrier carbocylization and Johnson-Claisen rearrangement, which was converted to iodide 2 by use of asymmetric alkylation and Sharpless epoxidation as key transformations. Coupling of iodide 2 and sulfone 3 furnished the C18-C34 fragment.

    Original languageEnglish
    Pages (from-to)5341-5352
    Number of pages12
    JournalTetrahedron
    Volume60
    Issue number25
    DOIs
    Publication statusPublished - 2004 Jun 14

    Keywords

    • Asymmetric alkylation
    • Ferrier carbocyclization
    • Johnson-Claisen rearrangement
    • Sulfone anion coupling

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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