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

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Date
11/2009
Author
Makiyi, Edward F.
Frade, Raquel F. M.
Lebl, Tomas
Jaffray, Ellis G.
Cobb, Susan E.
Harvey, Alan L.
Slawin, Alexandra M. Z.
Hay, Ronald T.
Westwood, Nicholas J.
Funder
The Royal Society
Grant ID
516002.K5682/kk
Keywords
Natural products
Total synthesis
Terpenoids
Cleavage reaction
Inflammation
NF-KAPPA-B
Sesquiterpene lactones
Natural-products
Drug Discovery
Constituents
Inhibition
QD Chemistry
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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)
Citation
Makiyi , E F , Frade , R F M , Lebl , T , Jaffray , E G , Cobb , S E , Harvey , A L , Slawin , A M Z , Hay , R T & Westwood , N J 2009 , ' Iso- seco -tanapartholides : isolation, synthesis and biological evaluation ' , European Journal of Organic Chemistry , vol. 2009 , no. 33 , pp. 5711-5715 . https://doi.org/10.1002/ejoc.200901016
Publication
European Journal of Organic Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1002/ejoc.200901016
ISSN
1434-193X
Type
Journal article
Rights
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim This is an open access article. Re-use of this article is permitted in accordance with the Terms and Conditions set out at http://wileyonlinelibrary.com/onlineopen#OnlineOpen_Terms
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/3420

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