Synthesis of Tamiflu

T. Mita; N. Fukuda; F. X. Roca; M. Kanai; M. Shibasaki

doi:10.1055/s-2007-968520

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Synfacts 2007(6): 0567-0567
DOI: 10.1055/s-2007-968520

Synthesis of Natural Products and Potential Drugs

Synthesis of Tamiflu

Contributor(s): Philip Kocienski
T. Mita, N. Fukuda, F. X. Roca, M. Kanai*, M. Shibasaki*
The University of Tokyo, Japan

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Publication History

Publication Date:
22 May 2007 (online)

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Significance

Tamiflu is a potent neuramidase inhibitor which is used for the treatment of the avian H5N1 virus. Key steps in the 15-step asymmetric synthesis depicted are (a) a catalytic asymmetric cleavage of meso-aziridine A with TMSN₃ and (b) a diastereoselective cyanophosphorylation of the enone E.