Docetaxel (Taxotere) derivatives: Novel NbCl3-based stereoselective approach to 2′-methyldocetaxel

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue , 1995, Pages 1811-1815

  Denis, Jean Noël ^a   Fkyerat, Abdellatif ^a   Gimbert, Yves ^a   Coutterez, Claire ^a   Mantellier, Pierre ^a   Jost, Sylvie ^a   Greene, Andrew E ^a  

^a UNIVERSITÉ JOSEPH FOURIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049077584     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/P19950001811     Document Type: Article

References (28)

1. S. Blechert and D. Guénard, in The Alkaloids, Chemistry and Pharmacology; ed. A. Brossi, Academic Press, San Diego, 1990, vol. 39, pp. 195-238
2. D. G. I. Kingston, G. Samaranayake and C. A. Ivey, J. Nat. Prod., 1990, 53, 1
3. D. G. I. Kingston, Pharmac. Ther., 1991, 52, 1
4. C. S. Swindell, Org. Prep. Proc. Int., 1991, 23, 465
5. S. Borman, Chem. Eng. News, 1991, 69(35), 11; 1992, 70(41), 30
6. P. Potier, D. Guénardand, F. Guéritte-Voegelein, Лес. Chem. Леї., 1993,26,160
7. F. Lavelle, F. Guéritte-Voegelein and D. Guénard, Bull. Cancer, 1993, 80, 326
8. D. G. I. Kingston, A. A. Molinero and J. M. Rimoldi, Prog. Chem. Org. Nat. Prod, 1993,61,1
9. M. Suffness, in Ann. Rep. Med. Chem.,ed. J. A. Bristol, Academic Press, San Diego, 1993; vol. 28, pp. 305-314
10. К. C. Nicolaou, W.-M. Dai and R. K. Guy, Angew. Chem., Int. Ed. Engl., 1994, 33, 15
11. G. I. Georg, S. M. Ali, J. Zygmunt and L. R. Jayasinghe, Exp. Opin. Ther. Patents, 1994, 4, 109.
12. For total syntheses of paclitaxel, see: K. C. Nicolaou, Z. Yang, J. J. Liu, H. Ueno, P. G. Nantermet, R. K. Guy, C. F. Claiborne, J. Renaud, E. A. Couladouros, K. Paulvannan and E. J. Sorensen, Nature, 1994, 367, 630
13. R. A. Holton, H-B. Kim, C. Somoza, F. Liang, R. J. Biediger, P. D. Boatman, M. Shindo, C. C. Smith, S. Kim, H. Nadizadeh, Y. Suzuki, C. Tao, P. Vu, S. Tang, P. Zhang, К. К. Murthi, L. N. Gentile and J. H. Liu, J. Am. Chem. Soc, 1994, 116, 1599.
14. E. J. Roskamp and S. F. Pedersen, J. Am. Chem. Soc, 1987, 109, 6551
15. For related work, see: J. B. Hartung and S. F. Pedersen, J. Am. Chem. Soc, 1989,109, 5468
16. E. J. Roskamp, P. S. Dragovich, J. B. Hartung and S. F. Pedersen, J. Org. Chem., 1989, 54, 4736
17. J. Szymoniak, J. Besançon and C. Moïse, Tetrahedron, 1992,48,3867;1994, 50, 2841
18. J. Szymoniak, L. Luque, J. Besançon and C. Moïse, Bull. Soc. Chim. Fr., 1994, 131, 89.
19. W. M. Pearlman, Tetrahedron Lett., 1967, 1663.
20. E. Didier, E. Fouque, I. Taillepied and A. Commerçon, Tetrahedron Lett., 1994, 35, 2349
21. A. M. Kanazawa, J-N. Denis and A. E. Greene, У. Org. Chem., 1994, 59, 1238
22. A. M. Kanazawa, J-N. Denis and A. E. Greene, J. Chem. Soc, Chem. Commun., 1994, 2591.
23. V. Sénilh, F. Guéritte, D. Guénard, M. Colin and P. Potier, C. R. Seances Acad. Sei., Ser. 2, 1984, 299, 1039.
24. K. Holmberg and В. Hansen, Acta Chem. Scand., Ser. A, 1979, 33, 410 and references cited therein.
25. S. Kim, J. I. Lee and Y. K. Ko, Tetrahedron Lett., 1984, 25, 4943
26. J-N. Denis, A. E. Greene, D. Guénard, F. Guéritte-Voegelein, L. Mangatal and P. Potier, J. Am. Chem. Soc, 1988, 110, 5917.
27. For a related example, see: A. Commerçon, D. Bézard, F. Bernard and J. D. Bourzat, Tetrahedron Lett., 1992, 33, 5185.
28. P. N. Devine, M. Reilly and T. Oh, Tetrahedron Lett., 1993, 34, 5827.