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

22 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

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Biological Products

Keywords

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

Cite this

Makiyi, E. F., Frade, R. F. M., Lebl, T., Jaffray, E. G., Cobb, S., Harvey, A. L., ... Hay, R. T. (2009). The iso-secoi-tanapartholides: isolation, synthesis and biological evaluation. Agewandte Chemie-International Edition, 2009(33), 5711-5715. https://doi.org/10.1002/ejoc.200901016
Makiyi, E.F. ; Frade, R.F.M. ; Lebl, T. ; Jaffray, E.G. ; Cobb, S. ; Harvey, Alan L. ; Slawin, A.M.Z. ; Hay, R.T. / The iso-secoi-tanapartholides: isolation, synthesis and biological evaluation. In: Agewandte Chemie-International Edition. 2009 ; Vol. 2009, No. 33. pp. 5711-5715.
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Makiyi, EF, Frade, RFM, Lebl, T, Jaffray, EG, Cobb, S, Harvey, AL, Slawin, AMZ & Hay, RT 2009, 'The iso-secoi-tanapartholides: isolation, synthesis and biological evaluation', Agewandte Chemie-International Edition, vol. 2009, no. 33, pp. 5711-5715. https://doi.org/10.1002/ejoc.200901016

The iso-secoi-tanapartholides: isolation, synthesis and biological evaluation. / Makiyi, E.F.; Frade, R.F.M.; Lebl, T.; Jaffray, E.G.; Cobb, S.; Harvey, Alan L.; Slawin, A.M.Z.; Hay, R.T.

In: Agewandte Chemie-International Edition, Vol. 2009, No. 33, 07.10.2009, p. 5711-5715.

Research output: Contribution to journalArticle

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AU - Makiyi, E.F.

AU - Frade, R.F.M.

AU - Lebl, T.

AU - Jaffray, E.G.

AU - Cobb, S.

AU - Harvey, Alan L.

AU - Slawin, A.M.Z.

AU - Hay, R.T.

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KW - total synthesis

KW - terpenoids

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KW - inflammation

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