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

Makiyi, E.F. and Frade, R.F.M. and Lebl, T. and Jaffray, E.G. and Cobb, S. and Harvey, Alan L. and Slawin, A.M.Z. and Hay, R.T. (2009) The iso-secoi-tanapartholides: isolation, synthesis and biological evaluation. Agewandte Chemie-International Edition, 2009 (33). pp. 5711-5715. ISSN 1433-7851

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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.