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Synfacts 2006(10): 0975-0975  
DOI: 10.1055/s-2006-949327
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Tamiflu

Contributor(s): Philip Kocienski
Y. Fukuta, T. Mita, N. Fukuda, M. Kanai*, M. Shibasaki*
The University of Tokyo, Japan
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Publikationsdatum:
21. September 2006 (online)

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Significance

Tamiflu (oseltamivir phosphate) is a potent neuramidase inhibitor which is used for the treatment of the avian H5N1 virus. Key steps in the 17-step asymmetric synthesis depicted include (a) a catalytic asymmetric cleavage of meso-aziridine A with TMSN3 and (b) a Ni(0)-catalyzed conjugate addition of TMSCN to enone E.