We thank the National Institutes of Health (GM 033049) and the National Science Foundation for their generous support of our programs. T.Z. thanks Novartis for a graduate fellowship. Mass spectra were provided, in part, by the Mass Spectrometry Regional Center of the University of California, San Francisco. Palladium salts were generously supplied by Johnson-Matthey. We are indebted to Dr. Kiran Guthikonda, David N. Zalatan, and Prof. Justin Du Bois for valuable discussions and donation of chemicals for the aziridination step. We thank Gilead Sciences for a reference sample of Tamiflu.
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Communication
A Concise Synthesis of (−)-Oseltamivir†
Article first published online: 10 APR 2008
DOI: 10.1002/anie.200800282
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Trost, Barry M. and Zhang, T. (2008), A Concise Synthesis of (−)-Oseltamivir. Angew. Chem. Int. Ed., 47: 3759–3761. doi: 10.1002/anie.200800282
- †
Publication History
- Issue published online: 28 APR 2008
- Article first published online: 10 APR 2008
- Manuscript Received: 19 JAN 2008
Funded by
- National Institutes of Health. Grant Number: GM 033049
- National Science Foundation
- Novartis
- Gilead Sciences
Keywords:
- aziridination;
- lactones;
- palladium;
- rhodium;
- total synthesis
Tackling the supply problem: A short and efficient synthesis of (−)-oseltamivir has been developed which requires eight steps from commercially available starting material and proceeds with an overall yield of 30 %. Key transformations include a novel palladium-catalyzed asymmetric allylic alkylation reaction (Pd-AAA, see scheme) as well as a chemo-, regio-, and stereoselective aziridination reaction. Phth=phthaloyl.