Stereoselective construction of the tricyclic core of neoliacinic acid

Clark, J.S. , Baxter, C.A., Dossetter, A.G., Poigny, S., Castro, J.L. and Whittingham, W.G. (2008) Stereoselective construction of the tricyclic core of neoliacinic acid. Journal of Organic Chemistry, 73(3), pp. 1040-1055. (doi:10.1021/jo702111u)

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Publisher's URL: http://dx.doi.org/10.1021/jo702111u

Abstract

The tricyclic core of the plant-derived sesquiterpene natural product neoliacinic acid was synthesized using a novel synthetic strategy. The pivotal synthetic transformations are construction of the key bicyclic ether-bridged intermediate by sequential deployment of metal carbenoid C−H insertion and ylide-forming reactions and installation of the lactone portion of neoliacinic acid by an acid-catalyzed intramolecular ring-opening reaction of an epoxide with a carboxylic acid.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Clark, Professor Stephen
Authors: Clark, J.S., Baxter, C.A., Dossetter, A.G., Poigny, S., Castro, J.L., and Whittingham, W.G.
Subjects:Q Science > QD Chemistry
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Journal of Organic Chemistry
Publisher:ACS American Chemical Society
ISSN:0022-3263

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