Work

A Redox Economical Synthesis of Bioactive 6,12-Guaianolides

Year: 2013

Type: article

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.

Source: Organic Letters

DOI: 10.1021/ol400904y

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

Institutions: University of Minnesota, University of Pittsburgh

Language: English

Topic: Sesquiterpenes and Asteraceae Studies

Subfield: Cancer Research

Field: Biochemistry, Genetics and Molecular Biology

Domain: Life Sciences

Open Access status: green

Funder: National Institute of General Medical Sciences

Awards: New Concepts, Methodologies and Scaffolds for Diversity-Oriented Organic Synthes, G2172971432, Allenic [2 + 2 + 1] Reactions Enabling Syntheses of Natural Products with 7-Membe