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Synlett 2009(15): 2473-2476  
DOI: 10.1055/s-0029-1217740
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile Access to Antiflu Agent Tamiflu/Oseltamivir

Hai Suna,b, Ying-Jie Linb, Yu-Lin Wu*a, Yikang Wu*a
a State Key Laboratory of Bioorganic & Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, P. R. of China
Fax: +86(21)64166128; e-Mail: ylwu@mail.sioc.ac.cn; e-Mail: yikangwu@mail.sioc.ac.cn;
b Department of Organic Chemistry, College of Chemistry, Jilin University, 2699 Qianjin Avenue, Changchun, Jilin 130012, P. R. of China
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Publication History

Received 16 June 2009
Publication Date:
27 August 2009 (online)

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A Facile Access to Antiflu Agent Tamiflu/OseltamivirSynlett 2009; 2009(17): 2884-2884
DOI: 10.1055/s-0029-1218288

Abstract

A practical approach to Tamiflu is developed featuring the construction of the carbocycle core of the target molecule through a Diels-Alder reaction with concurrent introduction of one of the nitrogen atoms. Incorporation of another nitrogen atom was achieved via a high-yielding regioselective ring opening of a cyclic sulfite.

Key words

Diels-Alder reactions - eliminations - enantiomeric ­resolution - epoxides - antiviral agents

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1

Information about avian flu and H5N1 virus can be found in: http://www.nature.com/avianflu/index.html.

13

The absolute configuration of (+)-10 was established by comparison of the spectroscopic data of the 15 thus derived with those reported in the literature (ref. 2k).