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Synfacts 2007(4): 0420-0420
DOI: 10.1055/s-2007-968327
DOI: 10.1055/s-2007-968327
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart · New York
Cu(I)-Mediated [3+3] Cycloaddition Reaction Delivering Tricyclic Alkaloid Scaffolds
M. Movassaghi*, B. Chen
Massachusetts Institute of Technology, Cambridge, USA
Further Information
Publication History
Publication Date:
23 March 2007 (online)
![](https://www.thieme-connect.de/media/synfacts/200704/lookinside/thumbnails/10.1055-s-2007-968327-1.jpg)
Significance
A new, extremely valuable method for the preparation of fused tricyclic alkaloid scaffolds is presented in this article. The desired tricyclic amino alcohols are synthesized in two steps via a novel CuBr×SMe2-mediated formal [3+3] cycloaddition reaction between cyclic enamines and enones and a subsequent reduction of the resulting imine with NaBH4. The addition proceeds with complete diastereoselectivity via a chair-like transition state which allows the simultaneous control of up to five stereocenters. An asymmetric organocatalytic variant is also proposed.