Synthesis of aspergillide A via proline-catalyzed trans-to-cis isomerization of a substituted tetrahydropyran

Tomohiro Nagasawa, Tomoo Nukada, Shigefumi Kuwahara

    Research output: Contribution to journalArticlepeer-review

    20 Citations (Scopus)

    Abstract

    The transformation of a common synthetic intermediate of aspergillides B and C into aspergillide A, a cytotoxin produced by a marine-derived fungus, has been accomplished in an eleven-step sequence involving an efficient proline-catalyzed isomerization of a 2,6-trans-substituted tetrahydropyran-2- acetaldehyde intermediate into the corresponding cis isomer and the Yamaguchi macrolactonization as the key steps.

    Original languageEnglish
    Pages (from-to)2882-2888
    Number of pages7
    JournalTetrahedron
    Volume67
    Issue number16
    DOIs
    Publication statusPublished - 2011 Apr 22

    Keywords

    • Aspergillide
    • Cytotoxic
    • Isomerization
    • Macrolide
    • Total synthesis

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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