Movassaghi, Mohammad and Ondrus, Alison E. (2005) Enantioselective Total Synthesis of Tricyclic Myrmicarin Alkaloids. Organic Letters, 7 (20). pp. 4423-4426. ISSN 1523-7060. PMCID PMC2992882. doi:10.1021/ol051629f. https://resolver.caltech.edu/CaltechAUTHORS:20170421-092258232
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Abstract
An enantioselective gram-scale synthesis of a key dihydroindolizine intermediate for the preparation of myrmicarin alkaloids is described. Key transformations in this convergent approach include a stereospecific palladium-catalyzed N-vinylation of a pyrrole with a vinyl triflate, a copper-catalyzed enantioselective conjugate reduction of a β-pyrrolyl enoate, and a regioselective Friedel−Crafts reaction. The synthesis of optically active and isomerically pure samples of (4aR)-myrmicarins 215A, 215B, and 217 in addition to their respective C4a-epimers is presented.
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| Additional Information: | © 2005 American Chemical Society. Received July 11, 2005. M.M. is a Dale F. and Betty Ann Frey Damon Runyon Scholar supported by the Damon Runyon Cancer Research Foundation (DRS-39-04). M.M. is a Firmenich Assistant Professor of Chemistry. A.E.O. acknowledges a Robert T. Haslam Presidential Graduate Fellowship. We acknowledge generous financial support by the donors of the American Chemical Society Petroleum Research Fund, MIT, Amgen Inc., and NIH-NIGMS (GM074825). | ||||||||||||||
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| Issue or Number: | 20 | ||||||||||||||
| PubMed Central ID: | PMC2992882 | ||||||||||||||
| DOI: | 10.1021/ol051629f | ||||||||||||||
| Record Number: | CaltechAUTHORS:20170421-092258232 | ||||||||||||||
| Persistent URL: | https://resolver.caltech.edu/CaltechAUTHORS:20170421-092258232 | ||||||||||||||
| Usage Policy: | No commercial reproduction, distribution, display or performance rights in this work are provided. | ||||||||||||||
| ID Code: | 76808 | ||||||||||||||
| Collection: | CaltechAUTHORS | ||||||||||||||
| Deposited By: | Donna Wrublewski | ||||||||||||||
| Deposited On: | 21 Apr 2017 17:20 | ||||||||||||||
| Last Modified: | 25 Apr 2022 20:40 |
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