We are grateful for financial support by NIH-NIGMS (GM074825). We thank Justin Kim, Owen Fenton, and Dr. Peter Müller for X-ray crystal structure analysis of 17⋅2 HCl.
A Concise and Versatile Double-Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma Alkaloids†
Article first published online: 12 MAR 2012
Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 51, Issue 19, pages 4572–4576, May 7, 2012
How to Cite
Medley, J. W. and Movassaghi, M. (2012), A Concise and Versatile Double-Cyclization Strategy for the Highly Stereoselective Synthesis and Arylative Dimerization of Aspidosperma Alkaloids . Angew. Chem. Int. Ed., 51: 4572–4576. doi: 10.1002/anie.201200387
- Issue published online: 3 MAY 2012
- Article first published online: 12 MAR 2012
- Manuscript Received: 15 JAN 2012
- NIH-NIGMS. Grant Number: GM074825
- total synthesis
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).