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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