We thank the NIH (GM52964) and the Welch Foundation for generous support. We also thank Dr. Joe Reibenspies for X-ray structural analysis, Francisco M. Torres for early studies in this project, and Prof. Justin Du Bois for helpful discussions.
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Communication
Enantioselective Synthesis of (+)-Monobromophakellin and (+)-Phakellin: A Concise Phakellin Annulation Strategy Applicable to Palau'amine†
Article first published online: 3 JAN 2008
DOI: 10.1002/anie.200703998
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Wang, S. and Romo, D. (2008), Enantioselective Synthesis of (+)-Monobromophakellin and (+)-Phakellin: A Concise Phakellin Annulation Strategy Applicable to Palau'amine. Angewandte Chemie International Edition, 47: 1284–1286. doi: 10.1002/anie.200703998
- †
Publication History
- Issue published online: 25 JAN 2008
- Article first published online: 3 JAN 2008
- Manuscript Received: 30 AUG 2007
Funded by
- NIH. Grant Number: GM52964
- Welch Foundation
Keywords:
- alkaloids;
- oxidative cyclization;
- palau'amine;
- total synthesis
Graphical Abstract
A unique oxidative cyclization of a tricycle bearing a guanidine aminal provides a concise route to the enantioselective synthesis of (+)-phakellin and (+)-monobromophakellin in nine and ten steps, respectively, starting from L-proline (see scheme). This sequence provides a simple annulation strategy applicable to the preparation of more complex members of this family of marine sponge-derived alkaloids including palau'amine.