Biomimetic total synthesis of (-)-erinacine E

Hideaki Watanabe, Masahisa Nakada

    Research output: Contribution to journalArticle

    38 Citations (Scopus)

    Abstract

    Biomimetic total synthesis of (-)-erinacine E (1) has been achieved starting from the enantiopure key intermediate, which was prepared via the convergent approach developed by us. The crucial step in this synthesis is an intramolecular aldol reaction driven by the 1,2-migration of a benzoyl group within a compound that was rationally designed to prevent the retro-aldol reaction, thereby successfully providing the strained skeleton of 1. Considering the structure of a putative biosynthetic intermediate, striatal A, the intramolecular aldol reaction driven by the C4′ acetyl group could be involved in the biosynthesis of 1. This acyl group migratory ring-closing reaction could be applied to the synthesis of other strained molecules.

    Original languageEnglish
    Pages (from-to)1150-1151
    Number of pages2
    JournalJournal of the American Chemical Society
    Volume130
    Issue number4
    DOIs
    Publication statusPublished - 2008 Jan 30

    Fingerprint

    Biomimetics
    Corpus Striatum
    Biosynthesis
    Skeleton
    Molecules
    erinacine E
    3-hydroxybutanal

    ASJC Scopus subject areas

    • Chemistry(all)

    Cite this

    Biomimetic total synthesis of (-)-erinacine E. / Watanabe, Hideaki; Nakada, Masahisa.

    In: Journal of the American Chemical Society, Vol. 130, No. 4, 30.01.2008, p. 1150-1151.

    Research output: Contribution to journalArticle

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