The iso-secoi-tanapartholides: isolation, synthesis and biological evaluation

E.F. Makiyi, R.F.M. Frade, T. Lebl, E.G. Jaffray, S. Cobb, Alan L. Harvey, A.M.Z. Slawin, R.T. Hay

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The isolation, identification and total synthesis of two plant-derived inhibitors of the NF-κB 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-κB signaling pathway.
Original languageEnglish
Pages (from-to)5711-5715
Number of pages4
JournalAgewandte Chemie-International Edition
Volume2009
Issue number33
DOIs
Publication statusPublished - 7 Oct 2009

Keywords

  • natural products
  • total synthesis
  • terpenoids
  • cleavage reaction
  • inflammation

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