A redox economical synthesis of bioactive 6,12-guaianolides
- PMID: 23662902
- PMCID: PMC3700414
- DOI: 10.1021/ol400904y
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 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.
Figures
References
-
- Drew DP, Krichau N, Reichwald K, Simonsen HT. Phytochem Rev. 2009;8:581–599.
-
- Science and Technology in Kazakhstan: Current Status and Future Prospects, 2006. National Research Council, Office for Central Europe and Eurasia; 2006.
-
- Ghantous A, Gali-Muhtasib H, Vuorela H, Saliba NA, Darwiche N. Drug Discov Today. 2010;15:668–678. - PubMed
-
- Rishton GM. Drug Discov Today. 1997;2:382–384. - PubMed
- Hogenauer K, Simic O, Antonello A, Hunger U, Smith MD, Ley SV. Chem Eur J. 2007;13:5688–5712. - PubMed
- Burns NZ, Baran PS, Hoffmann RW. Angew Chem Int Ed. 2009;48:2854–2867. - PubMed
- Grillet F, Huang C, Brummond KM. Org Lett. 2011;13:6304–6307. - PMC - PubMed
- Merfort I. Curr Drug Targets. 2011;12:1560–1573. - PubMed
Publication types
MeSH terms
Substances
Grants and funding
LinkOut - more resources
Full Text Sources
Other Literature Sources
