Novel asymmetric synthesis of oseltamivir phosphate (Tamiflu) from (-)-shikimic acid via cyclic sulfite intermediates

Tetrahedron Asymmetry

Volumn 22, Issue 16-17, 2011, Pages 1692-1699

  Nie, Liang Deng ^a   Shi, Xiao Xin ^a   Quan, Na ^a   Wang, Fei Feng ^a   Lu, Xia ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

OSELTAMIVIR; SHIKIMIC ACID;

ARTICLE; ASYMMETRIC SYNTHESIS; DRUG SYNTHESIS; PRIORITY JOURNAL; STEREOSPECIFICITY;

EID: 81155134626     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2011.09.014     Document Type: Article

References (60)

1. C.U. Kim, W. Lew, M.A. Williams, H. Wu, L. Zhang, X. Chen, P.A. Escarpe, D.B. Mendel, W.G. Laver, and R.C. Stevens J. Med. Chem. 41 1998 2451
2. C.U. Kim, W. Lew, M.A. Williams, H. Liu, L. Zhang, S. Swaminathan, N. Bischofberger, M.S. Chen, D.B. Mendel, C.Y. Tai, W.G. Laver, and R.C. Stevens J. Am. Chem. Soc. 119 1997 681
3. A.C. Hurt, P. Selleck, N. Komadina, R. Shaw, L. Brown, and I.G. Barr Antiviral Res. 73 2007 228
4. A. Abbott Nature 435 2005 407
5. G. Laver, and E. Garman Science 293 2001 1776
6. J.D. Bloom, L.I. Gong, and D. Baltimore Science 328 2010 1272
7. Magano J. Tetrahedron 67 2011 7875
8. M. Shibasaki, M. Kanai, and K. Yamatsugu Isr. J. Chem. 51 2011 316
9. J. Magano Chem. Rev. 109 2009 4398
10. M. Shibasaki, and M. Kanai Eur. J. Org. Chem. 2008 1839
11. S. Abrecht, M.C. Federspiel, H. Estermann, R. Fischer, M. Karpf, H.-J. Mair, T. Oberhauser, G. Rimmler, R. Trussardi, and U. Zutter Chimia 61 2007 93
12. V. Farina, and J.D. Brown Angew. Chem., Int. Ed. 45 2006 7330
13. S. Abrecht, P. Harrington, H. Iding, M. Karpf, R. Trussardi, B. Wirz, and U. Zutter Chimia 58 2004 621
14. B.M. Trost, and T. Zhang Chem. Eur. J. 17 2011 3630
15. T. Tanaka, Q. Tan, H. Kawakubo, and M. Hayashi J. Org. Chem. 76 2011 5477
16. S. Raghavan, and V.S. Babu Tetrahedron 67 2011 2044
17. Z. Hong, Q. Cui, J. Peng, H. Hu, and Z. Chen Chin. J. Chem. 28 2010 2479
18. S. Zhu, S. Yu, Y. Wang, and D. Ma Angew. Chem., Int. Ed. 49 2010 4656
19. H. Ishikawa, T. Suzuki, H. Orita, T. Uchimaru, and Y. Hayashi Chem. Eur. J. 16 2010 12616
20. J. Ma, Y. Zhao, S. Ng, J. Zhang, J. Zeng, A. Than, P. Chen, and X.-W. Liu Chem. Eur. J. 16 2010 4533
21. L. Werner, A. Machara, and T. Hudlicky Adv. Synth. Catal. 352 2010 195
22. H. Osato, I.L. Jones, A. Chen, and C.L.L. Chai Org. Lett. 12 2010 60
23. J.S. Ko, J.E. Keum, and S.Y. Ko J. Org. Chem. 75 2010 7006
24. A. Kamimura, and T. Nakano J. Org. Chem. 75 2010 3133
25. J. Weng, Y.-B. Li, R.-B. Wang, F.-Q. Li, C. Liu, A.S.C. Chan, and G. Lu J. Org. Chem. 75 2010 3125
26. P. Wichienukul, S. Akkarasamiyo, N. Kongkathip, and B. Kongkathip Tetrahedron Lett. 51 2010 3208
27. M. Karpf, and R. Trussardi Angew. Chem., Int. Ed. 48 2009 5760
28. B. Sullivan, I. Carrera, M. Drouin, and T. Hudlicky Angew. Chem., Int. Ed. 48 2009 4229
29. H. Ishikawa, T. Suzuki, and Y. Hayashi Angew. Chem., Int. Ed. 48 2009 1304
30. K. Yamatsugu, L. Yin, S. Kamijo, Y. Kimura, M. Kanai, and M. Shibasaki Angew. Chem., Int. Ed. 48 2009 1070
31. L.-D. Nie, and X.-X. Shi Tetrahedron: Asymmetry 20 2009 124
32. L.-D. Nie, X.-X. Shi, K.H. Ko, and W.-D. Lu J. Org. Chem. 74 2009 3970
33. K. Yamatsugu, M. Kanai, and M. Shibasaki Tetrahedron 65 2009 6017
34. N. Satoh, T. Akiba, S. Yokoshima, and T. Fukuyama Tetrahedron 65 2009 3239
35. Y. Kimura, K. Yamatsugu, M. Kanai, N. Echigo, T. Kuzuhara, and M. Shibasaki Tetrahedron Lett. 50 2009 3205
36. T. Oshitari, and T. Mandai Synlett 2009 787
37. T. Mandai, and T. Oshitari Synlett 2009 783
38. H. Sun, Y.-J. Lin, Y.-L. Wu, and Y. Wu Synlett 2009 2473
39. J.-J. Shie, J.-M. Fang, and C.-H. Wong Angew. Chem., Int. Ed. 47 2008 5788
40. B.M. Trost, and T. Zhang Angew. Chem., Int. Ed. 47 2008 3759
41. N.T. Kipassa, H. Okamura, K. Kina, T. Hamada, and T. Iwagawa Org. Lett. 10 2008 815
42. U. Zutter, H. Iding, P. Spurr, and B. Wirz J. Org. Chem. 73 2008 4895
43. M. Matveenko, A.C. Willis, and M.G. Banwell Tetrahedron Lett. 49 2008 7018
44. M. Morita, T. Sone, K. Yamatsugu, Y. Sohtome, S. Matsunaga, M. Kanai, Y. Watanabe, and M. Shibasaki Bioorg. Med. Chem. Lett. 18 2008 600
45. 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, and C.-H. Wong J. Am. Chem. Soc. 129 2007 11892
46. N. Satoh, T. Akiba, S. Yokoshima, and T. Fukuyama Angew. Chem., Int. Ed. 46 2007 5734
47. K.M. Bromfield, H. Graden, D.P. Hagberg, T. Olsson, and N. Kann Chem. Commun. 2007 3183
48. T. Mita, N. Fukuda, F.X. Roca, M. Kanai, and M. Shibasaki Org. Lett. 9 2007 259
49. K. Yamatsugu, S. Kamijo, Y. Suto, M. Kanai, and M. Shibasaki Tetrahedron Lett. 48 2007 1403
50. Y. Fukuta, T. Mita, N. Fukuda, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 128 2006 6312
51. Y.-Y. Yeung, S. Hong, and E.J. Corey J. Am. Chem. Soc. 128 2006 6310
52. X. Cong, and Z.-J. Yao J. Org. Chem. 71 2006 5365
53. P.J. Harrington, J.D. Brown, T. Foderaro, and R.C. Hughes Org. Process Res. Dev. 8 2004 86
54. M. Karpf, and R. Trussardi J. Org. Chem. 66 2001 2044
55. M. Federspiel, R. Fischer, M. Hennig, H.-J. Mair, T. Oberhauser, G. Rimmler, T. Albiez, J. Bruhin, H. Estermann, C. Gandert, V. Gockel, S. Gotzo, U. Hoffmann, G. Huber, G. Janatsch, S. Lauper, O. Rockel-Stabler, R. Trussardi, and A.G. Zwahlen Org. Process Res. Dev. 3 1999 266
56. 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, and L. Zhang J. Org. Chem. 63 1998 4545
57. H.-S. Byun, L. He, and R. Bittman Tetrahedron 56 2000 7051
58. B.B. Lohray Synthesis 1992 1035
59. Y.G. Gololobov, and L.F. Kasukhin Tetrahedron 48 1992 1353
60. J.E. Leffler, and R.D. Temple J. Am. Chem. Soc. 89 1967 5235