Asymmetric synthesis and in vivo biological inactivity of the right-hand terpenoid fragment of terpendole e

Masato Oikawa, Ryo Hashimoto, Makoto Sasaki

    Research output: Contribution to journalArticle

    11 Citations (Scopus)

    Abstract

    Synthesis of the DEF-ring terpenoid fragment of terpendole E, an Eg5 inhibitor, is described. The DE-ring was constructed by a modification of Barrero's radical cyclization. The F-ring tetrahydropyran was then constructed by acid-induced cyclization of an epoxy alcohol, which was prepared by cross-metathesis followed by Shi's epoxidation. Cell-based assays indicated that the DEF-ring fragment is not capable of inhibiting cell growth and cell cycle progression of human cancer cell lines, indicating that the DEF-ring fragment alone is not sufficient for the biological activity. The DEF-ring terpenoid fragment of terpendole E, has been synthesized in 15 steps starting from farnesyl acetate, employing radical cyclization (DE-ring formation) and stereoselective cyclization of an epoxyalcohol (F-ring formation). Cell-based assays showed that the right-hand DEF-ring fragment is inactive in cell growth and cell cycle progression of human cancer cell lines.

    Original languageEnglish
    Pages (from-to)538-546
    Number of pages9
    JournalEuropean Journal of Organic Chemistry
    Issue number3
    DOIs
    Publication statusPublished - 2011 Jan 1

    Keywords

    • Cyclization
    • Inhibitors
    • Metathesis
    • Natural products
    • Radical reactions
    • Reduction
    • Terpenoids

    ASJC Scopus subject areas

    • Physical and Theoretical Chemistry
    • Organic Chemistry

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