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

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 ?-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-?B inhibitors such as cumambrin A and indeed were shown to inhibit NF-?B signaling and cancer cell growth.

SUBMITTER: Wen B

PROVIDER: S-EPMC3700414 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature

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

Wen Bo B Hexum Joseph K JK Widen John C JC Harki Daniel A DA Brummond Kay M KM

Organic letters 20130510 11

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. ...[more]

PMID: 23662902

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