Synthesis of (-)-oseltamivir phosphate (tamiflu) starting from cis-2,3-bis(hydroxymethyl)aziridine

Journal of Organic Chemistry

Volumn 77, Issue 19, 2012, Pages 8792-8796

  Oh, Hong Se ^a   Kang, Han Young ^a  

^a Chungbuk National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

AZIRIDINES; BOC GROUP; CYCLIC PRODUCTS; DESYM-METRIZATION; KEY REACTIONS; NITROGEN ATOM; OSELTAMIVIR; RING CLOSING METATHESIS; STEREOGENIC CENTERS; TAMIFLU;

METHANOL;

IONIC LIQUIDS;

AZIRIDINE DERIVATIVE; CIS 2,3 BIS(HYDROXYMETHYL)AZIRIDINE; NITROGEN; OSELTAMIVIR; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; ATOM; DRUG SYNTHESIS; RING CLOSING METATHESIS;

ALKYLATION; AZIRIDINES; CATALYSIS; CYCLIZATION; MOLECULAR STRUCTURE; OSELTAMIVIR; STEREOISOMERISM;

EID: 84867358396     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3015853     Document Type: Article

References (32)

1. von Itzstein, M. Nat. Rev. Drug Discovery 2007, 6, 967
2. Moscona, A. N. Engl. J. Med. 2005, 353, 1363
3. Magano, J. Chem. Rev. 2009, 109, 4398
4. Nie, L.-D.; Shi, X.-X. Tetrahedron: Asymmetry 2009, 20, 124
5. Ishikawa, H.; Suzuki, T.; Hayashi, Y. Angew. Chem. 2009, 121, 1330
6. Angew. Chem., Int. Ed. 2009, 48, 1304.
7. Nie, L.-D.; Shi, X.-X.; Ko, K. H.; Lu, W.-D. J. Org. Chem. 2009, 74, 3970
8. Satoh, N.; Akiba, T.; Yokoshima, S.; Fukuyama, T. Tetrahedron 2009, 65, 3239
9. Weng, J.; Li, Y.-B.; Wang, R.-B.; Li, F.-Q.; Liu, C.; Chan, A. S. C.; Lu, G. J. Org. Chem. 2010, 75, 3125
10. Kamimura, A.; Nakano, T. J. Org. Chem. 2010, 75, 3133
11. Ma, J.; Zhao, Y.; Ng, S.; Zhang, J.; Zeng, J.; Than, A.; Chen, P.; Liu, X.-W. Chem.-Eur. J. 2010, 16, 4533
12. Osato, H.; Jones, I. L.; Chen, A.; Chai, C. L. L. Org. Lett. 2010, 12, 60
13. Wichienukul, P.; Akkarasamiyo, S.; Kongkathip, N.; Kongkathip, B. Tetrahedron Lett. 2010, 51, 3208
14. Nakano, H.; Osone, K.; Takeshita, M.; Kwon, E.; Seki, C.; Matsuyama, H.; Takano, N.; Kohari, Y. Chem. Commun. 2010, 46, 4827
15. Zhu, S.; Yu, S.; Wang, Y.; Ma, D. Angew. Chem., Int. Ed. 2010, 49, 4656
16. Ko, J. S.; Keum, J. E.; Ko, S. Y. J. Org. Chem. 2010, 75, 7006
17. Ishikawa, H.; Suzuki, T.; Orita, H.; Uchimaru, T.; Hayashi, Y. Chem.-Eur. J. 2010, 16, 12616
18. Tanaka, T.; Tan, Q.; Kawakubo, H.; Hayashi, M. J. Org. Chem. 2011, 76, 5477
19. Ishikawa, H.; Bondzic, B. P.; Hayashi, Y. Eur. J. Org. Chem. 2011, 6020
20. Aziridines and Epoxides in Organic Synthesis; Yudin, A. K., Ed.; Wiley-VCH: Weinheim, 2006.
21. Fukuta, Y.; Mita, T.; Fukuda, N.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2006, 128, 6312
22. Mita, T.; Fukuda, N.; Roca, F. X.; Kanai, M.; Shibasaki, M. Org. Lett. 2007, 9, 259
23. Fuji, K.; Kawabata, T.; Kiryu, Y.; Sugiura, Y.; Taga, T.; Miwa, Y. Tetrahedron Lett. 1990, 31, 6663
24. Davoli, P.; Forni, A.; Moretti, I.; Prati, F.; Torre, G. Tetrahedron. 2001, 57, 1801
25. Metathesis in Natural Product Synthesis; Cossy, J.; Arseniyadis, S.; Meyer, C., Eds.; Wiley-VCH: Weinheim, 2010.
26. Davoli, P.; Caselli, E.; Bucciarelli, M.; Forni, A.; Torre, G.; Prati, F. J. Chem. Soc., Perkin Trans. 1 2002, 1948
27. Mehta, G.; Islam, K. Tetrahedron Lett. 2004, 45, 3611
28. Takabe, K.; Hashimoto, H.; Sugimoto, H.; Nomoto, M.; Yoda, H. Tetrahedron: Asymmetry 2004, 15, 909
29. Kameda, Y.; Nagano, H. Tetrahedron 2006, 62, 9751
30. Richter, F.; Bauer, M.; Perez, C.; Maichle-Mössmer, C.; Maier, M. E. J. Org. Chem. 2002, 67, 2474
31. Kinsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J., Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791
32. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168