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Synfacts 2013; 9(1): 0002
DOI: 10.1055/s-0032-1317719
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of (–)-Oseltamivir Phosphate

Contributor(s):
Philip Kocienski
Oh H.-S, Kang H.-Y * Chungbuk National University, Republic of Korea
Synthesis of (–)-Oseltamivir Phosphate (Tamiflu) Starting from cis-2,3-Bis(hydroxymethyl)aziridine.

J. Org. Chem. 2012;
77: 8792-8796
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

oseltamivir phosphate - Tamiflu - enzymatic desymmetrization - ring-closing metathesis - aziridine ring opening

Significance

Oseltamivir phosphate (Tamiflu®) is a neuraminidase inhibitor that is widely prescribed for the treatment of various influenzas. The key step in this small-scale, 21-step synthesis is the enzymatic desymmetrization of the meso-diol A using Amano lipase PS. The diol A was prepared in six steps starting from cis-2-butene-1,4-diol.


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Comment

For the enzymatic desymmetrization of closely related substrates, see: K. Fuji et al. Tetrahedron Lett. 1990, 31, 6663. For a closely related strategy based on epoxide opening and ring-closing metathesis, see: V. Rawat, S. Dey, A. Sudalai, Org. Biomol. Chem. 2012, 10, 3988.


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