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 journalArticle

17 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 26 2013

Fingerprint Dive into the research topics of 'A redox economical synthesis of bioactive 6,12-guaianolides'. Together they form a unique fingerprint.

  • Cite this

    Wen, B., Hexum, J. K., Widen, J. C., Harki, D. A., & Brummond, K. M. (2013). A redox economical synthesis of bioactive 6,12-guaianolides. Organic Letters, 15(11), 2644-2647. https://doi.org/10.1021/ol400904y