This research was supported financially in part by a grant for the 21st Century COE Program and a Grant-in-Aid (15109001 and 16073205) from the Ministry of Education, Culture, Sports, Science, and Technology of Japan. We are indebted to Dr. Kunisuke Izawa of Ajinomoto Co. for an ample supply of D-phenylalanine.
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A Practical Synthesis of (−)-Oseltamivir†
Article first published online: 26 JUN 2007
DOI: 10.1002/anie.200701754
Copyright © 2007 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Additional Information
How to Cite
Satoh, N., Akiba, T., Yokoshima, S. and Fukuyama, T. (2007), A Practical Synthesis of (−)-Oseltamivir. Angew. Chem. Int. Ed., 46: 5734–5736. doi: 10.1002/anie.200701754
- †
Publication History
- Issue published online: 13 JUL 2007
- Article first published online: 26 JUN 2007
- Manuscript Received: 20 APR 2007
Funded by
- 21st Century COE Program
- Grant-in-Aid. Grant Numbers: 15109001, 16073205
Keywords:
- antiviral agents;
- Diels–Alder reaction;
- domino reactions;
- lactones;
- rearrangement
Keep it simple: Still in hot demand, the influenza drug (−)-oseltamivir phosphate (tamiflu; see scheme) has now been synthesized from pyridine by using inexpensive reagents. A strict minimum of purification steps are required in a synthetic route which features an asymmetric Diels–Alder reaction, a bromolactonization, a Hofmann rearrangement, and a domino transformation of a bicyclo[2.2.2] system into an aziridine intermediate.