Published September 29, 2005
| Accepted Version + Supplemental Material
Journal Article
Open
Enantioselective Total Synthesis of Tricyclic Myrmicarin Alkaloids
- Creators
- Movassaghi, Mohammad
-
Ondrus, Alison E.
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.
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).Attached Files
Accepted Version - nihms60802.pdf
Supplemental Material - ol051629fsi20050817_062240.pdf
Files
nihms60802.pdf
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Additional details
- PMCID
- PMC2992882
- Eprint ID
- 76808
- Resolver ID
- CaltechAUTHORS:20170421-092258232
- DRS-39-04
- Damon Runyon Cancer Research Foundation
- Robert T. Haslam Presidential Graduate Fellowship
- American Chemical Society Petroleum Research Fund
- MIT
- Amgen Inc.
- GM074825
- NIH
- Created
-
2017-04-21Created from EPrint's datestamp field
- Updated
-
2022-04-25Created from EPrint's last_modified field