A Concise and Versatile Double-Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma Alkaloids
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Movassaghi_A concise and versatile.pdf
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1.52 MB
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Author(s)
Medley, Jonathan William
Movassaghi, Mohammad
Date Issued
May 2012
Journal
Angewandte Chemie International Edition
Publisher
Wiley Blackwell
Citation
Medley, Jonathan William, and Mohammad Movassaghi. “A Concise and Versatile Double-Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma Alkaloids.” Angewandte Chemie International Edition 51, no. 19 (May 7, 2012): 4572-4576.
Version
Author's final manuscript
Abstract
Building cycles: A strategy for the concise, stereoselective synthesis of aspidosperma alkaloids and related structures via a common putative diiminium ion intermediate is reported. The approach enables the dimerization of aspidosperma-type structures at the sterically hindered C2 position. The intermediate is prepared in one step from the shown lactam through an electrophilic double-cyclization cascade (see scheme; Tf=trifluoromethanesulfonyl).
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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Creative Commons Attribution-Noncommercial-Share Alike 3.0
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DOI of Published Version
https://doi.org/10.1002/anie.201200387
