We thank the University of California for financial support as well as the UCSD Mass Spectrometry Facility and UCSD Small Molecule X-Ray Facility.
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Communication
An Ugi Reaction in the Total Synthesis of (−)-Dysibetaine†
Article first published online: 27 JAN 2009
DOI: 10.1002/anie.200805709
Copyright © 2009 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 48, Issue 10, pages 1845–1848, February 23, 2009
Additional Information
How to Cite
Isaacson, J. and Kobayashi, Y. (2009), An Ugi Reaction in the Total Synthesis of (−)-Dysibetaine. Angew. Chem. Int. Ed., 48: 1845–1848. doi: 10.1002/anie.200805709
- †
Publication History
- Issue published online: 17 FEB 2009
- Article first published online: 27 JAN 2009
- Manuscript Received: 21 NOV 2008
Funded by
- University of California
Keywords:
- betaines;
- isocyanides;
- natural products;
- total synthesis;
- Ugi reaction
Abstract
(−)-Dysibetaine has been synthesized in 11 steps from readily available L-malic acid (see scheme). The key step is a unique Ugi 4-center-3-component cyclization reaction, where an ester group acts as the carboxylic acid component. The use of 1,1,1,3,3,3-hexamethyldisilazane as an ammonia equivalent and a specially designed isocyanide leads to an expeditious synthesis.