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Synfacts 2009(7): 0705-0705  
DOI: 10.1055/s-0029-1217249
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Tamiflu (Oseltamivir)

Contributor(s): Philip Kocienski
H. Ishikawa, T. Suzuki, Y. Hayashi*
Tokyo University of Science, Japan
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Publication History

Publication Date:
22 June 2009 (online)

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Significance

A remarkably short and efficient synthesis of (-)-oseltamivir is reported featuring an organocatalytic Michael addition (100% yield) as the first step. The sequence requires only three one-pot operations and proceeds in 57% overall yield from the nitroalkene B. The three one-pot operations involved the conversions of (1) B to G, (2) G to H and (3) H to oseltamivir.