Expeditious access to (-)-shikimic acid derivatives for Tamiflu synthesis

Tetrahedron Letters

Volumn 52, Issue 48, 2011, Pages 6352-6354

  Osato, Hiroshi ^a   Jones, Ian L ^b   Goh, Huini ^c   Chai, Christina L L ^b   Chen, Anqi ^b  

^a SHIONOGI AND CO LTD   (Japan)

^b INSTITUTE OF CHEMICAL AND ENGINEERING SCIENCES   (Singapore)

^c NANYANG TECHNOLOGICAL UNIVERSITY   (Singapore)

Author keywords

Bernet Vasella reaction; D Ribose; Ring closing olefin metathesis; Shikimic acid; Tamiflu

Indexed keywords

OSELTAMIVIR; RIBOSE; SHIKIMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; DRUG SYNTHESIS; ONE POT SYNTHESIS; RING CLOSING METATHESIS;

EID: 80255140458     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.09.035     Document Type: Article

References (26)

1. Hoffmann, U.; Huber, G.; Janatsch, G.; Lauper, S.; Rockel-Stabler, O.; Trussardi, R.; Zwahlen, A. G. Org. Process Res. Dev. 1999, 3, 266.
2. Guo, J.; Frost, J. W. Org. Lett. 2004, 6, 1585.
3. Guo, J.; Frost, J. W. US 2007/0190621A1, 16/08/2007.; Chem. Abstr. 2007, 147, 275841.
4. (a) Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990;
5. (b) Nakane, M.; Hutchinson, C. R.; Gollman, H. Tetrahedron Lett. 1980, 21, 1213;
6. (c) Fürstner, A.; Jumbam, D.; Teslic, J.; Weidmann, H. J. Org. Chem. 1991, 56, 2213.
7. (a) Enserink, M. Science 2006, 312, 382;
8. (b) Farina, V.; Brown, J. D. Angew. Chem., Int. Ed. 2006, 45, 7330.
9. (a) Magano, J. Chem. Rev. 2009, 109, 4398;
10. (b) Osato, H.; Jones, I. L.; Chen, A.; Chai, C. L. L. Org. Lett. 2010, 12, 60. and references therein;
11. (c) Werner, L.; Machara, A.; Hudlicky, T. Adv. Synth. Catal. 2010, 352, 195;
12. (d) Ma, J.; Zhao, Y.; Ng, S.; Zhang, J.; Zeng, J.; Than, A.; Chen, P.; Liu, X.-W. Chem. Eur. J. 2010, 16, 4533;
13. (e) Ko, J. S.; Keum, J. E.; Ko, S. Y. J. Org. Chem. 2010, 75, 7006;
14. (f) 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;
15. (g) Kamimura, A.; Nakano, T. J. Org. Chem. 2010, 75, 3133;
16. (h) Zhu, S.; Yu, S.; Wang, Y.; Ma, D. Angew. Chem., Int. Ed. 2010, 49, 4656;
17. (i) Pawinee, W.; Sunisa, A.; Ngampong, K.; Boonsong, K. Tetrahedron Lett. 2010, 51, 3208;
18. (j) Sadagopan, R.; Babu, S. V. Tetrahedron 2011, 67, 2044;
19. (k) Trost, B. M.; Zhang, T. Chem. Eur. J. 2011, 17, 3630.
20. Federspiel, M.; Fisher, R.; Henning, M.; Mair, H. J.; Oberhauser, T.; Rimmler, G.; Albiez, T.; Bruhin, J.; Estermann, H.; Gandert, C.; Gockel, V.; Gotzo, S.; Carnell, A.J.; Head, R.; Bassett, D.; Schneider, M. Tetrahedron: Asymmetry 2004, 15, 821.
21. Dijkstra, G.; Kruizinga, W. H.; Kellogg, R. M.J. Org. Chem. 1987, 52, 4230.
22. (a) Albert, R.; Dax, K.; Link, R. W.; Stütz, A. E. Carbohydr. Res. 1983, 118,118;
23. (b) Guo, H.; O'Doherty, G. A. J. Org. Chem. 2008, 73, 5211;
24. (c) Balskus, E. P.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 6810.
25. Nie, L.-D.; Shi, X.-X. Tetrahedron: Asymmetry 2009, 20, 124.
26. Kancharla, P. K.; Doddi, V. R.; Kokatla, H.; Vankar, Y. D. Tetrahedron Lett. 2009, 50, 6951.