A concise and flexible synthesis of the potent anti-influenza agents tamiflu and tamiphosphor

Angewandte Chemie - International Edition

Volumn 47, Issue 31, 2008, Pages 5788-5791

  Shie, Jiun Jie ^b   Fang, Jim Min ^a,b   Wong, Chi Huey ^b  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

^b GENOMICS RESEARCH CENTER   (Taiwan)

Author keywords

Asymmetric synthesis; Chiral pool; Drug design; Synthesis design; Total synthesis

Indexed keywords

ASYMMETRIC SYNTHESIS; CHIRAL POOL; DRUG DESIGN; SYNTHESIS DESIGN; TOTAL SYNTHESIS;

CARBONYLATION; CHEMICAL REACTIONS; PALLADIUM;

SYNTHESIS (CHEMICAL);

ACETAMIDE DERIVATIVE; ANTIVIRUS AGENT; CYCLOHEXENE DERIVATIVE; OSELTAMIVIR; TAMIPHOSPHOR;

ARTICLE; HUMAN; INFLUENZA; SYNTHESIS;

ACETAMIDES; ANTIVIRAL AGENTS; CYCLOHEXENES; HUMANS; INFLUENZA, HUMAN; OSELTAMIVIR;

EID: 53549123019     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200801959     Document Type: Article

References (46)

1. a) 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, R. C. Stevens, J. Am. Chem. Soc. 1997, 119, 681-690;
2. b) W. Lew, X. Chen, C. U. Kim, Curr. Med. Chem. 2000, 7, 663-672;
3. c) K. McClellan, C. M. Perry, Drugs 2001, 61, 263-283.
4. a) Patient information sheet from the US Food and Drug Administration, March 10, 2008;
5. b) I. Fuyuno, Nature 2007, 446, 358-359.
6. 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, 11892-11893.
7. a) 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, R. C. Stevens, J. Am. Chem. Soc. 1997, 119, 681-690;
8. b) 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, 4545-4550;
9. c) 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, 266-274.
10. For reviews of methods used in tamiflu synthesis, see: a) S. Abrecht, P. Harrington, H. Iding, M. Karpf, R. Trussardi, B. Wirz, U. Zutter, Chimia 2004, 58, 621-629;
11. b) V. Farina, J. D. Brown, Angew. Chem. 2006, 118, 7488-7492;
12. Angew. Chem. Int. Ed. 2006, 45, 7330-7334;
13. c) S. Abrecht, M. C. Federspiel, H. Estermann, R. Fisher, M. Karpf, H.-J. Mair, T. Oberhauser, G. Rimmler, R. Trussardi, U. Zutter, Chimia 2007, 61, 93-99;
14. d) M. Shibasaki, M. Kanai, Eur. J. Org. Chem. 2008, 1839-1850.
15. a) K. Yamatsugu, S. Kamijo, Y. Suto, M. Kanai, M. Shibasaki, Tetrahedron Lett. 2007, 48, 1403-1406;
16. b) Y. Fukuta, T. Mita, N. Fukuda, M. Kanai, M. Shibasaki, J. Am. Chem. Soc. 2006, 128, 6312-6313;
17. c) T. Mita, N. Fukuda, F. X. Roca, M. Kanai, M. Shibasaki, Org. Lett. 2007, 9, 259-262;
18. d) M. Morita, T. Sone, K. Yamatsugu, Y. Sohtome, S. Matsunaga, M. Kanai, Y. Watanabe, M. Shibasaki, Bioorg. Med. Chem. Lett. 2008, 18, 600-602.
19. Y.-Y. Yeung, S. Hong, E. J. Corey, J. Am. Chem. Soc. 2006, 128, 6310-6311.
20. N. Satoh, T. Akiba, S. Yokoshima, T. Fukuyama, Angew. Chem. 2007, 119, 5836-5838;
21. Angew. Chem. Int. Ed. 2007, 46, 5734-5736.
22. K. M. Bromfield, H. Gradén, D. P. Hagberg, T. Olsson, N. Kann, Chem. Commun. 2007, 3183-3185.
23. B. M. Trost, T. Zhang, Angew. Chem. 2008, 120, 3819-3821;
24. Angew. Chem. Int. Ed. 2008, 47, 3759-3761.
25. a) G. W. J. Fleet, T. K. M. Shing, J. Chem. Soc. Chem. Commun. 1983, 849-850;
26. b) G. W. J. Fleet, T. K. M. Shing, S. M. Warr, J. Chem. Soc. Perkin 1 1984, 905-908;
27. c) H. Streicher, J. Meisch, C. Bohner, Tetrahedron 2001, 57, 8851-8859;
28. d) H. Streicher, C. Bohner, Tetrahedron 2002, 58, 7573-7581;
29. e) B. K. Radatus, K. S. K. Murthy, G. Weeratunga, S. F. Horne, K. K. Kothakonda, E. C. G. Wolf, Z. Wang, US patent 20080009639 application, 2008.
30. a) D. R. Boyd, G. N. Sheldrake, Nat. Prod. Rep. 1998, 15, 309-324;
31. b) T. Hudlicky, D. Gonzalez, D. T. Gibson, Aldrichimica Acta 1999, 32, 35-62;
32. c) M. A. Endoma, V. P. Bui, J. Hansen, T. Hudlicky, Org. Process Res. Dev. 2002, 6, 525-532;
33. d) M. G. Banwell, A. J. Edwards, G. J. Harfoot, K. A. Jolliffe, M. D. McLeod, K. J. McRae, S. G. Stewart, M. Vögtle, Pure Appl. Chem. 2003, 75, 223-229;
34. e) R. A. Johnson, Org. React. 2004, 63, 117-264.
35. Y.-Y. Yeung, X. Gao, E. J. Corey, J. Am. Chem. Soc. 2006, 128, 9644-9645.
36. a) S. Greenberg, J. G. Moffatt, J. Am. Chem. Soc. 1973, 95, 4016-4025;
37. b) D. R. Boyd, N. D. Sharma, C. R. O'Dowd, F. Hempenstall, Chem. Commun. 2000, 2151-2152;
38. c) D. R. Boyd, N. D. Sharma, N. M. Llamas, J. F. Malone, C. R. O'Dowd, C. C. R. Allen, Org. Biomol. Chem. 2005, 3, 1953-1963;
39. d) D. R. Boyd, N. D. Sharma, N. M. Llamas, J. F. Malone, C. R. O'Dowd, C. C. R. Allen, Org. Biomol. Chem. 2006, 4, 2208-2217.
40. A. J. Blacker, R. J. Booth, G. M. Davies, J. K. Sutherland, J. Chem. Soc. Perkin Trans. 1 1995, 2861-2870.
41. B. Bessièrea, A. Schoenfelder, C. Verrat, A. Mann, P. Ornstein, C. Pedregal, Tetrahedron Lett. 2002, 43, 7659-7662.
42. a) M. Karpf, R. Trusardi, J. Org. Chem. 2001, 66, 2044-2051;
43. b) P. Harrington, J. D. Brown, T. Foderaro, R. C. Hughes, Org. Process Res. Dev. 2004, 8, 86-91.
44. B. Akhlaghinia, Synthesis 2005, 1955-1958.
45. J. L. Humphreys, D. J. Lowes, K. A. Wesson, R. C. Whitehead, Tetrahedron 2006, 62, 5099-5108.
46. N. A. Bumagin, K. V. Nikitin, I. P. Beletskaya, J. Organomet. Chem. 1988, 358, 563-565.