Iso-seco-tanapartholides: isolation, synthesis and biological evaluation

Edward F. Makiyi, Raquel F. M. Frade, Tomas Lebl, Ellis G. Jaffray, Susan E. Cobb, Alan L. Harvey, Alexandra M. Z. Slawin, Ronald T. Hay, Nicholas J. Westwood

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    25 Citations (Scopus)

    Abstract

    The isolation, identification and total synthesis of two plant-derived inhibitors of the NF-kappa B signaling pathway from the iso-seco-tanapartholide family of natural products is described. A key step in the efficient reaction sequence is a late-stage oxidative cleavage reaction that was carried out in the absence of protecting groups to give the natural products directly. A detailed comparison of the synthetic material with samples of the natural products proved informative. Biological studies on synthetic material confirmed that these compounds act late in the NF-kappa B signaling pathway. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

    Original languageEnglish
    Pages (from-to)5711-5715
    Number of pages5
    JournalEuropean Journal of Organic Chemistry
    Issue number33
    DOIs
    Publication statusPublished - Nov 2009

    Keywords

    • Natural products
    • Total synthesis
    • Terpenoids
    • Cleavage reaction
    • Inflammation
    • NF-KAPPA-B
    • SESQUITERPENE LACTONES
    • NATURAL-PRODUCTS
    • DRUG DISCOVERY
    • CONSTITUENTS
    • INHIBITION

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