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Synfacts 2007(11): 1129-1129  
DOI: 10.1055/s-2007-991198
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (-)-Oseltamivir

Contributor(s): Philip Kocienski
N. Satoh, T. Akiba, S. Yokoshima, T. Fukuyama*
The University of Tokyo, Japan
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Publication History

Publication Date:
23 October 2007 (online)

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Significance

This synthesis of the potent neuraminidase inhibitor (-)-oseltamivir phosphate (tamiflu) features an enantioselective Diels-Alder reaction to generate the azabicyclo[2.2.2]octane system D. The lactone E (er > 99:1) was purified by crystallization from MeOH.