Efficient preparation of the key intermediate in corey's tamiflu synthesis

Chinese Journal of Chemistry

Volumn 28, Issue 12, 2010, Pages 2479-2483

  Hong, Zhangyong ^a   Cui, Qi ^a   Peng, Jiannan ^a   Hu, Huan ^a   Chen, Zeming ^a  

^a NANKAI UNIVERSITY   (China)

Author keywords

avian influenza; inhibitors; multifunctional catalyst; synthesis design; Tamiflu

Indexed keywords

EID: 78651322087     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201190025     Document Type: Article

References (26)

1. Farina, V.,;, Brown, J. D.,. Angew. Chem., Int. Ed., 2006, 45, 7330.
2. Taubenberger, J. K.,;, Reid, A. H.,;, Fanning, T. G.,. Virology, 2000, 274, 241.
3. Kim, C. U.,;, Lew, W.,;, Williams, M. A.,;, Liu, H.,;, Zhang, L.,;, Swaminathan, S.,;, Bischofberger, N.,;, Chen, M. S.,;, Mendel, D. B.,;, Tai, C. Y.,;, Laver, W. G.,;, Stevens, R. C.,. J. Am. Chem. Soc., 1997, 119, 681.
4. Moscona, A.,. New Engl. J. Med., 2005, 353, 1363.
5. Russell, R. J.,;, Haire, L. F.,;, Stevens, D. J.,;, Collins, P. J.,;, Lin, Y. P.,;, Blackburn, G. M.,;, Hay, A. J.,;, Gamblin, S. J.,;, Skehel, J. J.,. Nature (London), 2006, 443, 45.
6. Reece, P. A.,. J. Med. Virol., 2007, 79, 1577.
7. Albrecht, S.,;, Harrington, P.,;, Iding, H.,;, Karpf, M.,;, Trussardi, R.,;, Wirz, B.,;, Zutter, U.,. Chimia, 2004, 58, 621.
8. Yeung, Y.-Y.,;, Hong, S.,;, Corey, E. J.,. J. Am. Chem. Soc., 2006, 128, 6310.
9. Fukuta, Y.,;, Mita, T.,;, Fukuda, N.,;, Kanai, M.,;, Shibasaki, M.,. J. Am. Chem. Soc., 2006, 128, 6312.
10. Cong, X.,;, Yao, Z.-J.,. J. Org. Chem., 2006, 71, 5365.
11. Mita, T.,;, Fukuda, N.,;, Roca, F. X.,;, Kanai, M.,;, Shibasaki, M.,. Org. Lett., 2007, 9, 259.
12. Yamatsugu, K.,;, Kamijo, S.,;, Suto, Y.,;, Kanai, M.,;, Shibasaki, M.,. Tetrahedron Lett., 2007, 48, 1403.
13. Satoh, N.,;, Akiba, T.,;, Yokoshima, S.,;, Fukuyama, T.,. Angew. Chem., Int. Ed., 2007, 46, 5734.
14. Bromfield, K. M.,;, Grade'n, H.,;, Hagberg, D. P.,;, Olsson, H.,;, Kann, N.,. Chem. Commun., 2007, 3183.
15. Kraus, G. A.,;, Goronga, T.,. Synthesis, 2007, 1765.
16. Trost, B. M.,;, Zhang, T.,. Angew. Chem., Int. Ed., 2008, 47, 3759.
17. For a recent review on the supply problem and syntheses of oseltamivir, see
18. Farina, V.,;, Brown, J. D.,. Angew. Chem., Int. Ed., 2006, 45, 7330.
19. Shibasaki, M.,;, Kanai, M.,. Eur. J. Org. Chem., 2008, 1839.
20. Sun, H.,;, Lin, Y.,;, Wu, Y.,;, Wu, Y.,. Chin. J. Org. Chem., 2009, 29, 1869.
21. Kipassa, N. T.,;, Okamura, H.,;, Kina, K.,;, Hamada, T.,;, Iwagawa, T.,. Org. Lett., 2008, 10, 815.
22. This compound can also be prepared with 65% yield in two steps according to the published procedure:, Emerman, S. L,;, Meinwald, J.,. J. Org. Chem., 1956, 21, 375.
23. For works about one pot, see
24. Yu, B.,;, Yang, Z.,;, Cao, H.,. Curr. Org. Chem., 2005, 9, 179.
25. Yu, B.,;, Xie, J.,;, Deng, S.,;, Hui, Y.,. J. Am. Chem. Soc., 1999, 121, 12196.
26. Wang, Y.,;, Ye, X.-S.,;, Zhang, L.-H.,. Org. Biomol. Chem., 2007, 5, 2189.