Quinine is an alkaloid natural product isolated from the bark of the cinchona tree. It has long served as a synthetic target due to its antimalarial properties. The total synthesis of quinine can be envisioned employing a recently developed catalytic enone cycloallylation methodology. This new process merges phosphine organocatalysis and transition metal catalysis. The pursuit of quinine details the first application of this novel method in organic synthesis. Herein, phosphine-catalyzed transformations of [alpha, beta]-unsaturated compounds as well as a historical overview of the alkaloid target are thoroughly reviewed. The following chapters discuss both racemic and asymmetric approaches toward quinine, including the completion of a formal synthesis. Not only has the cycloallylation proved successful in this synthetic application, but this body of work has seen the development of many highly selective transformations. / text
| Identifer | oai:union.ndltd.org:UTEXAS/oai:repositories.lib.utexas.edu:2152/17816 |
| Date | 07 September 2012 |
| Creators | Webber, Peter Andrew, 1981- |
| Source Sets | University of Texas |
| Language | English |
| Detected Language | English |
| Format | electronic |
| Rights | Copyright is held by the author. Presentation of this material on the Libraries' web site by University Libraries, The University of Texas at Austin was made possible under a limited license grant from the author who has retained all copyrights in the works. |
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