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Org Lett. 2013 Jun 7;15(11):2644-7. doi: 10.1021/ol400904y. Epub 2013 May 10.

A redox economical synthesis of bioactive 6,12-guaianolides.

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1
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.

Abstract

Syntheses of two 6,12-guaianolide analogs are reported within. The scope of the tandem allylboration/lactonization chemistry is expanded to provide a functionalized allene-yne-containing α-methylene butyrolactone that undergoes a Rh(I)-catalyzed cyclocarbonylation reaction to afford a 5-7-5 ring system. The resulting cycloadducts bear a structural resemblance to other NF-κB inhibitors such as cumambrin A and indeed were shown to inhibit NF-κB signaling and cancer cell growth.

PMID:
23662902
PMCID:
PMC3700414
DOI:
10.1021/ol400904y
[Indexed for MEDLINE]
Free PMC Article

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