A redox economical synthesis of bioactive 6,12-guaianolides

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

doi:10.1021/ol400904y

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 journal › Article › peer-review

21 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 language	English (US)
Pages (from-to)	2644-2647
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	11
DOIs	https://doi.org/10.1021/ol400904y
State	Published - Jun 7 2013

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AU - Wen, Bo

AU - Hexum, Joseph K.

AU - Widen, John C.

AU - Harki, Daniel A.

AU - Brummond, Kay M.

PY - 2013/6/7

Y1 - 2013/6/7

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AB - 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.

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A redox economical synthesis of bioactive 6,12-guaianolides

Abstract

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