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Synfacts 2006(10): 0974-0974  
DOI: 10.1055/s-2006-949328
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Tamiflu

Contributor(s): Philip Kocienski
Y.-Y. Yeung, S. Hong, E. J. Corey*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
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 10-step asymmetric synthesis depicted include (a) an efficient asymmetric Diels-Alder reaction mediated by an enantiopure catalyst and (b) a stereoselective electrophilic addition of N-bromo­acetamide to an alkene mediated by SnBr4.