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Synfacts 2011(1): 0007-0007  
DOI: 10.1055/s-0030-1258977
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Oseltamivir

Contributor(s): Philip J. Kocienski
J. S. Ko, J. E. Keum, S. Y. Ko*
Ewha Womans University, Seoul, Korea
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Publication History

Publication Date:
21 December 2010 (online)

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Significance

Oseltamivir is an orally active neuraminidase inhibitor prescribed for the treatment of various influenzas. The key step in this small-scale, 16-step synthesis (7.1% overall from d-mannitol) is the intramolecular aldol reaction of lactone E to give the bicyclic derivative F in 76% yield as a single diastereoisomer.