Synthesis of aspergillide A from a synthetic intermediate of aspergillide B

Tomohiro Nagasawa, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    28 Citations (Scopus)

    Abstract

    The first synthesis of aspergillide A, a cytotoxin produced by a marine-derived fungus, has been achieved from a synthetic intermediate of aspergillide B by using a proline-mediated epimerization of a 2,6-trans-substituted tetrahydropyran-2-acetaldehyde intermediate into the corresponding cis-isomer via a retro-oxy-Michael/oxy-Michael sequence as the key transformation.

    Original languageEnglish
    Pages (from-to)875-877
    Number of pages3
    JournalTetrahedron Letters
    Volume51
    Issue number5
    DOIs
    Publication statusPublished - 2010 Feb 3

    Keywords

    • Aspergillide
    • Cytotoxic
    • Epimerization
    • Macrolide

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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