Stereodivergent Synthesis and Configurational Assignment of the C1-C15 Segment of Amphirionin-5

Moemi Kanto, Sota Sato, Masashi Tsuda, Makoto Sasaki

    Research output: Contribution to journalArticlepeer-review

    7 Citations (Scopus)

    Abstract

    The relative configuration of the C3-C12 portion of amphirionin-5, a novel marine polyketide with potent cell proliferation-promoting activity, was established by the stereodivergent synthesis of six diastereomeric model compounds and comparison of their NMR spectroscopic data with those reported for the natural product. This study led to the elucidation of the relative configuration between C4/C5 and C9/C12 and to the reassignment of the proposed configuration of the C9 position of amphirionin-5.

    Original languageEnglish
    Pages (from-to)9105-9121
    Number of pages17
    JournalJournal of Organic Chemistry
    Volume81
    Issue number19
    DOIs
    Publication statusPublished - 2016 Oct 7

    ASJC Scopus subject areas

    • Organic Chemistry

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