A redox economical synthesis of bioactive 6,12-guaianolides

Bo Wen, Joseph K. Hexum, John C. Widen, Daniel A. Harki, Kay M. Brummond

Research output: Contribution to journalArticlepeer-review

19 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)2644-2647
Number of pages4
JournalOrganic Letters
Volume15
Issue number11
DOIs
StatePublished - Jun 7 2013

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