Enantioselective synthesis of oseltamivir phosphate

Tetrahedron

Volumn 67, Issue 11, 2011, Pages 2044-2050

  Raghavan, Sadagopan ^a   Babu, Vaddela Sudheer ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Asymmetric Diels Alder reaction; Iodolactonization; Mitsunobu reaction; Selenoxide elimination; Tamiflu

Indexed keywords

AZIDE; AZIRIDINE; BENZOIC ACID; CARBAMIC ACID; EPOXIDE; ESTER; FUKUTIN; OSELTAMIVIR; REAGENT; TRIMETHYLSILYL DERIVATIVE;

ARTICLE; CONTROLLED STUDY; DIELS ALDER REACTION; DRUG SYNTHESIS; ENANTIOSELECTIVITY; EPOXIDATION; MITSUNOBU REACTION; NONHUMAN; PRIORITY JOURNAL;

ALNUS;

EID: 79952038512     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2011.01.064     Document Type: Article

References (62)

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. A.C. Schmidt Drugs 64 2004 2031
3. A. Moscona N. Engl. J. Med. 353 2005 1363
4. R.J. Russell, L.F. Haire, D.J. Stevens, P.J. Collins, Y.P. Lin, G.M. Blackburn, A.J. Hay, S.J. Gamblin, and J.J. Skehel Nature (London) 443 2006 45
5. 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
6. 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
7. M. Karpf, and R. Trussardi J. Org. Chem. 66 2001 2044 and references therein
8. P.J. Harrington, J.D. Brown, T. Foderaro, and R.C. Hughes Org. Process Res. Dev. 8 2004 86
9. 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
10. M. Karpf, and R. Trussardi J. Org. Chem. 66 2001 2044
11. X. Cong, and Z.-J. Yao J. Org. Chem. 71 2006 5365
12. Y.-Y. Yeung, S. Hong, and E.J. Corey J. Am. Chem. Soc. 128 2006 6310
13. Y. Fukuta, T. Mita, N. Fukuda, M. Kanai, and M. Shibasaki J. Am. Chem. Soc. 128 2006 6312
14. J.-J. Shie, J.-M. Fang, S.-Y. Wang, K.-C. Tasi, Y.-S.E. Cheng, A.-S. Yang, S.-C. Hsiao, C.-Y. Su, and C.-H. Wong J. Am. Chem. Soc. 129 2007 11892
15. N. Satoh, T. Akiba, S. Yokoshima, and T. Fukuyama Angew. Chem., Int. Ed. 46 2007 5734
16. K. Yamatsugu, S. Kamijo, Y. Suto, M. Kanai, and M. Shibasaki Tetrahedron Lett. 48 2007 1403
17. K.M. Bromfield, H. Graden, D.P. Hagberg, T. Olsson, and N. Kann Chem. Commun. 2007 3183
18. T. Mita, N. Fukuda, F.X. Roca, M. Kanai, and M. Shibasaki Org. Lett. 9 2007 259
19. N.T. Kipassa, H. Okamura, K. Kina, T. Hamada, and T. Iwagawa Org. Lett. 10 2008 815
20. U. Zutter, H. Iding, P. Spurr, and B. Wirz J. Org. Chem. 73 2008 4895
21. M. Matveenko, A.C. Willis, and M.G. Banwell Tetrahedron Lett. 49 2008 7018
22. J.-J. Shie, J.-M. Fang, and C.-H. Wong Angew. Chem., Int. Ed. 47 2008 5788
23. B.M. Trost, and T. Zhang Angew. Chem., Int. Ed. 47 2008 3759
24. H. Ishikawa, T. Suzuki, and Y. Hayashi Angew. Chem., Int. Ed. 48 2009 1304
25. K. Yamatsugu, L. Yin, S. Kamijo, Y. Kimura, M. Kanai, and M. Shibasaki Angew. Chem., Int. Ed. 48 2009 1070
26. T. Mandai, and T. Oshitari Synlett 2009 783
27. T. Oshitari, and T. Mandai Synlett 2009 787
28. B. Sullivan, I. Carrera, M. Drouin, and T. Hudlicky Angew. Chem., Int. Ed. 48 2009 4229
29. L.-D. Nie, and X.-X. Shi Tetrahedron: Asymmetry 20 2009 124
30. L.-D. Nie, X.-X. Shi, K.H. Ho, and W.-D. Lu J. Org. Chem. 74 2009 3970
31. M. Karpf, and R. Trussardi Angew. Chem., Int. Ed. 48 2009 5760
32. J. Weng, Y.-B. Li, R.-B. Wang, F.-Q. Feng-Quan Li, C. Liu, A.S.C. Chan, and G. Lu J. Org. Chem. 75 2010 3125
33. H. Ishikawa, and Y. Hayashi Fain Kemikaru 39 2010 5
34. H. Ishikawa, and Y. Hayashi Kagaku to Seibutsu 48 2010 156
35. L. Werner, A. Machara, and T. Hudlicky Adv. Synth. Catal. 352 2010 195
36. For a review see: J. Magano Chem. Rev. 109 2009 4398
37. T. Poll, J.O. Metter, and G. Helmchen Angew. Chem. 97 1985 116
38. T. Poll, A. Sebezak, H. Hartmann, and G. Helmchen Tetrahedron Lett. 26 1985 3095
39. E.J. Corey, and H.-C. Huang Tetrahedron Lett. 30 1989 5235
40. B.M. Trost, and T.R. Verhoeven J. Am. Chem. Soc. 102 1980 4730
41. T. Fukuyama, M. Cheung, and T. Kan Synlett 1999 1301
42. J.R. Henry, L.R. Marcin, M.C. McIntosh, P.M. Scola, G.D. Harris Jr., and S.M. Weinreb Tetrahedron Lett. 30 1989 5709
43. N2 fashion without epimerization as understood from the amide, prepared from the amine obtained by deprotection of 9 and (S)-methoxy mandelic acid.
44. S.C. Miller, and T.S. Scanlan J. Am. Chem. Soc. 119 1997 2301
45. P. Kocovsky, and I. Stary J. Org. Chem. 55 1990 3236
46. D.B. Berkowitz, and M.L. Pedersen J. Org. Chem. 60 1995 5368
47. A. Jenmalm, W. Berts, K. Luthman, I. Csoreg, and U. Hacksell J. Org. Chem. 60 1995 1026
48. A. Jenmalm, and K. Luthman Tetrahedron Lett. 39 1998 3213
49. M. Caron, and K.B. Sharpless J. Org. Chem. 50 1985 1560
50. D. Sinou, and M. Emziane Tetrahedron Lett. 27 1986 4423
51. 1H NMR spectra of the corresponding acetates, the methine protons appeared δ 4.95 as a dt (J=3.8, 9.1 Hz) and at δ 4.7 as a dd (J=4.4, 10.3 Hz), respectively.
52. K.C. Nicolaou, Y.-L. Zhong, and P.S. Baran J. Am. Chem. Soc. 122 2000 7596
53. K.C. Nicolaou, T. Montagnon, and P.S. Baran Angew. Chem., Int. Ed. 41 2002 993
54. 2, see: H.J. Reich, J.M. Renga, and I.L. Reich J. Am. Chem. Soc. 97 1975 5434
55. A single isomer was observed, however, its structure was not assigned.
56. The trimethylsilyl group suffered deprotection probably during workup.
57. The selenenylation proceeded in poor yield (30%) using substrate 11.
58. After 36 h compounds 16 and 17 were isolated in a 3:1 ratio, respectively.
59. Y. Ittah, Y. Sasson, I. Shahak, S. Isaroom, and J. Blum J. Org. Chem. 43 1978 4271
60. D. Tanner, and P. Somfai Tetrahedron Lett. 28 1987 1211
61. Structure was not assigned to compound 23.
62. After 36 h compounds 18 and 24 were isolated in a 3:2 ratio, respectively.