High-yielding synthesis of the anti-influenza neuramidase inhibitor (-)-oseltamivir by three "One-Pot" operations

Angewandte Chemie - International Edition

Volumn 48, Issue 7, 2009, Pages 1304-1307

  Ishikawa, Hayato ^a   Suzuki, Takaki ^a   Hayashi, Yujiro ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

Antiviral agents; Domino reactions; Organocatalysis; Oseltamivir; Tamiflu

Indexed keywords

CATALYSIS; RATE CONSTANTS; SYNTHESIS (CHEMICAL);

ANTIVIRAL AGENTS; DOMINO REACTIONS; ORGANOCATALYSIS; OSELTAMIVIR; TAMIFLU;

REACTION KINETICS;

ANTIVIRUS AGENT; DIPHENYLPROLINOL SILYL ETHER; DRUG DERIVATIVE; ETHER DERIVATIVE; OSELTAMIVIR; PROLINE;

ANIMAL; ARTICLE; CATALYSIS; CHEMISTRY; HUMAN; INFLUENZA; STEREOISOMERISM; SYNTHESIS;

ANIMALS; ANTIVIRAL AGENTS; CATALYSIS; ETHERS; HUMANS; INFLUENZA, HUMAN; OSELTAMIVIR; PROLINE; STEREOISOMERISM;

EID: 60149095699     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200804883     Document Type: Article

References (64)

1. V. Farina, J. D. Brown, Angew. Chem. 2006, 118, 7488;
2. Angew. Chem. Int. Ed. 2006, 45, 7330.
3. C.U. Kim, W. Lew, M. A. Williams, H. Liu, L. Zhang, S. Swaminathan, N. Bishofberger, M. S. Chen, D. B. Mendel, C. Y. Tai, W. G. Laver, R. C. Stevens, J. Am. Chem. Soc. 1997, 119, 681.
4. P. J. Collins, L. F. Haire, Y. P. Lin, J. Liu, R. J. Russell, P. A. Walker, J. J. Skehel, S. R. Martin, A. J. Hay, S. J. Gamblin, Nature 2008, 453, 1258.
5. a) J. C. Rohloff, K. M. Kent, M. J. Postich, M. W. Becker, H. H. Chapman, D. E. Kelly, W. Lew, M. S. Louie, L. R. McGee, E. J. Prisbe, L. M. Schultze, R. H. Yu, L. Zhang, J. Org. Chem. 1998, 63, 4545;
6. b) M. Federspiel, R. Fischer, M. Hennig, H.-J. Mair, T. Oberhauser, G. Rimmler, T. Albiez, J. Bruhin, H. Estermann, C. Gandert, V. Göckel, S. Götzö, U. Hoffmann, G. Huber, G. Janatsch, S. Lauper, O. Röckel-Stäbler, R. Trussardi, A. G. Zwahlen, Org. Process Res. Dev. 1999, 3, 266;
7. c)P. J. Harrington, J. D. Brown, T. Foderaro, R. C. Hughes, Org. Process Res. Dev. 2004, 8, 86;
8. d)S. Abrecht, P. Harrington, H. Iding, M. Karpf, R. Trussardi, B. Wirz, U. Zutter, Chimia 2004, 58, 621;
9. e) Y.-Y. Yeung, S. Hong, E. J. Corey, J. Am. Chem. Soc. 2006, 128, 6310;
10. f) Y. Fukuta, T. Mita, N. Fukuda, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 6312;
11. g) X. Cong, Z.-J. Yao, J. Org. Chem. 2006, 71, 5365;
12. h) S. Abrecht, M. C. Federspiel, H. Estermann, R. Fischer, M. Karpf, H.-J. Mair, T. Oberhauser, G. Rimmler, R. Trussardi, U. Zutter, Chimia 2007, 61, 93;
13. i) N. Satoh, T. Akiba, S. Yokoshima, T. Fukuyama, Angew. Chem. 2007, 119, 5836;
14. Angew. Chem. Int. Ed. 2007, 46, 5734;
15. j) J.-J. Shie, J.-M. Fang, S.-Y. Wang, K.-C. Tsai, Y.-S. E. Cheng, A.-S. Yang, S.-C. Hsiao, C.-Y. Su, C.-H. Wong, J. Am. Chem. Soc. 2007, 129, 11892;
16. k) T. Mita, N. Fukuda, F. X. Roca, M. Kanai, M. Shibasaki, Org. Lett. 2007, 9, 259;
17. l) U. Zutter, H. Iding, P. Spurr, B. Wirz, J. Org. Chem. 2008, 73, 4895;
18. m) J.-J. Shie, J.-M. Fang, C.-H. Wong, Angew. Chem. 2008, 120, 5872;
19. Angew. Chem. Int. Ed. 2008, 47, 5788;
20. n) B. M. Trost, T. Zhang, Angew. Chem. 2008, 120, 3819;
21. Angew. Chem. Int. Ed. 2008, 47, 3759;
22. o) Review, see; M. Shibasaki, M. Kanai, Eur. J. Org. Chem. 2008, 1839.
23. Reviews on organocatalysis, see: a) P. I. Dalko, L. Moisan, Angew. Chem. 2004, 116, 5248;
24. Angew. Chem. Int. Ed. 2004, 43, 5138;
25. b) Asymmetric Organocatalysis (Eds.: A. Berkessel, H. Groger), Wiley-VCH, Weinheim, 2005;
26. c) Y. Hayashi, J. Syn. Org. Chem. Jpn. 2005, 63, 464;
27. d) B. List, Chem. Commun. 2006, 819;
28. e) M. Marigo, K. A. Jørgensen, Chem. Commun. 2006, 2001;
29. f) M. J. Gaunt, C. C. C. Johnsson, A. McNally, N. T. Vo, Drug Discovery Today 2007, 12, 8;
30. g)Enantioselective Organocatalysis (Ed.: P.I. Dalko), Wiley-VCH, Weinheim, 2007;
31. h) C. F. Barbas III, Angew. Chem. 2008, 120, 44;
32. Angew. Chem. Int. Ed. 2008, 47, 42;
33. i) A. Dondoni, A. Massi, Angew. Chem. 2008, 120, 4716;
34. Angew. Chem. Int. Ed. 2008, 47, 4638;
35. j) P. Melchiorre, M. Marigo, A. Carlone, G. Bartoli, Angew. Chem. 2008, 120, 6232;
36. Angew. Chem. Int. Ed. 2008, 47, 6138.
37. Reviews, see: a) C. Palomo, A. Mielgo, Angew. Chem. 2006, 118, 8042;
38. Angew. Chem. Int. Ed. 2006, 45, 7876;
39. b) A. Mielgo, C. Palomo, Chem. Asian J. 2008, 3, 922.
40. a) Y. Hayashi, H. Gotoh, T. Hayashi, M. Shoji, Angew. Chem. 2005, 117, 4284;
41. Angew. Chem. Int. Ed. 2005, 44, 4212;
42. b) H. Gotoh, R. Masui, H. Ogino, M. Shoji, Y. Hayashi, Angew. Chem. 2006, 118, 7007;
43. Angew. Chem. Int. Ed. 2006, 45, 6853;
44. c) H. Gotoh, Y. Hayashi, Org. Lett. 2007, 9, 2859;
45. d) Y. Hayashi, T. Okano, S. Aratake, D. Hazelard, Angew. Chem. 2007, 119, 5010;
46. Angew. Chem. Int. Ed. 2007, 46, 4922;
47. e) H. Gotoh, H. Ishikawa, Y. Hayashi, Org. Lett. 2007, 9, 5307;
48. f) Y. Hayashi, H. Gotoh, R. Masui, H. Ishikawa, Angew. Chem. 2008, 120, 4076;
49. Angew. Chem. Int. Ed. 2008, 47, 4012;
50. g) Y. Hayashi, S. Samanta, H. Gotoh, H. Ishikawa, Angew. Chem. 2008, 120, 6736;
51. Angew. Chem. Int. Ed. 2008, 47, 6634;
52. h) Y. Hayashi, T. Itoh, M. Ohkubo, H. Ishikawa, Angew. Chem. 2008, 120, 4800;
53. Angew. Chem. Int. Ed. 2008, 47, 4722;
54. i) Y. Hayashi, T. Okano, T. Itoh, T. Urushima, H. Ishikawa, T. Uchimaru, Angew. Chem. 2008, 120, 9193;
55. Angew. Chem. Int. Ed. 2008, 47, 9053.
56. a) M. Marigo, T. C. Wabnitz, D. Fielenbach, K. A. Jørgensen, Angew. Chem. 2005, 117, 804;
57. Angew. Chem. Int. Ed. 2005, 44, 794;
58. b) M. Marigo, D. Fielenbach, A. Braunton, A. Kjasgaard, K. A. Jørgensen, Angew. Chem. 2005, 117, 3769;
59. Angew. Chem. Int. Ed. 2005, 44, 3703. Recent report, see;
60. c) P. T. Franke, R. L. Johansen, S. Bertelsen, K. A. Jørgensen, Chem. Asian J. 2008, 3, 216.
61. D. Enders, M. R. M. Huttl, C. Grondal, G. Raabe, Nature 2006, 441, 861.
62. a) C. Naegeli, A. Tyabji, Helv. Chim. Acta 1934, 17, 931;
63. b) E. R. Barnum, C. S. Hamilton, J. Am. Chem. Soc. 1942, 64, 540;
64. c) J. B. Press, C. M. Hofmann, S. R. Safir, J. Org. Chem. 1979, 44, 3292.