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Enantioselective Total Synthesis of Tricyclic Myrmicarin Alkaloids

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.

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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.

Item Type:Article
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URLURL TypeDescription CentralArticle Info
Ondrus, Alison E.0000-0002-6023-3290
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).
Funding AgencyGrant Number
Damon Runyon Cancer Research FoundationDRS-39-04
Robert T. Haslam Presidential Graduate FellowshipUNSPECIFIED
American Chemical Society Petroleum Research FundUNSPECIFIED
Issue or Number:20
PubMed Central ID:PMC2992882
Record Number:CaltechAUTHORS:20170421-092258232
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Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:76808
Deposited By: Donna Wrublewski
Deposited On:21 Apr 2017 17:20
Last Modified:25 Apr 2022 20:40

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