An efficient semisynthesis of 7-deoxypaclitaxel from taxine

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 1, 2001, Pages 59-65

  Saičić, Radomir N ^a   Matović, Radomir ^b  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITY OF BELGRADE   (Serbia)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 52549119999     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (38)

1. M. C. Wani, H. L. Taylor, M. E. Wall, P. Coggon and A. T. McPhail, J. Am. Chem. Soc., 1971, 93, 2325.
2. (a) The Chemistry and Pharmacology of Taxol and its Derivatives, ed. V. Farina, Elsevier, Amsterdam, 1995;
3. R: Science and Applications, ed. M. Suffness, CRC Press, Boca Raton, 1995, and references cited therein;
4. (c) K. C. Nicolaou, W.-M. Dai and R. K. Guy, Angew. Chem., Int. Ed. Engl., 1994, 33, 15;
5. Angew. Chem., 1994, 106, 38.
6. (a) K. C. Nicolaou, H. Ueno, J.-J. Liu, P. G. Nantermet, Z. Yang, J. Renaud, K. Paulvannan and R. Chadha, J. Am. Chem. Soc., 1995, 117, 653, and references therein;
7. (b) 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, K. K. Murthi, L. N. Gentile and J. H. Liu, J. Am. Chem. Soc., 1994, 116, 1599, and references therein;
8. (c) S. J. Danishefsky, J. J. Masters, W. B. Young, J. T. Link, L. B. Snyder, T. V. Magee, D. K. Jung, R. C. A. Isaacs, W. G. Bornmann, C. A. Alaimo, C. A. Coburn and M. J. Di Grandi, J. Am. Chem. Soc., 1996, 118, 2843;
9. (d) P. A. Wender, N. F. Badham, S. P. Conway, P. E. Floreancig, T. E. Glass, J. B. Houze, N. E. Krauss, D. Lee, D. G. Marquess, P. I. McGrane, W. Meng, M. G. Natchus, A. J. Shuker, J. C. Sutton and R. E. Taylor, J. Am. Chem. Soc., 1997, 119, 2757, and references therein;
10. (e) T. Mukaiyama, I. Shiina, H. Iwadare, M. Saitoh, T. Nishimura, N. Ohkawa, H. Sakoh, K. Nishimura, Y. Tani, M. Hasegawa, K. Yamada and K. Saitoh, Chem. Eur. J., 1999, 5, 121;
11. (f) K. Morihara, R. Hara, S. Kawahara, T. Nishimori, N. Nakamura, H. Kusama and I. Kuwajima, J. Am. Chem. Soc., 1998, 120, 12980.
12. J.-N. Denis, A. E. Greene, D. Guenard, F. Gueritte-Voegelein, L. Mangatal and P. Potier, J. Am. Chem. Soc., 1988, 110, 5917.
13. D. Guenard, F. Gueritte-Voegelein and P. Potier, Acc. Chem. Res., 1993, 26, 160.
14. (a) G. Chauviere, D. Guenard, F. Picot, V. Senilh and P. Potier, C. R. Seances Acad. Sci., Ser. 2, 1981, 293, 501;
15. (b) K. M. Witherup, S. A. Look, M. W. Stasko, T. J. Ghiorzi, G. M. Mushik and G. M. Cragg, J. Nat. Prod., 1990, 53, 1249;
16. (c) ref. 4.
17. (a) H. Lucas, Arch. Pharm., 1856, 14, 438;
18. (b) G. Appendino, in Alkaloids: Chemical and Biological Perspectives, ed. S. W. Pelletier, Pergamon, 1996, vol. 11, p. 237;
19. (c) L. H. D. Jenniskens, E. L. M. van Rosendaal, T. A. van Beek, P. H. G. Wiegerinck and H. W. Scheeren, J. Nat. Prod., 1996, 59, 117;
20. (d) for an alternative isolation procedure see ref. 10a.
21. (a) L. Ettouati, A. Ahond, C. Poupat and P. Potier, J. Nat. Prod., 1991, 54, 1455;
22. -1, 10 g being taxine B; we are grateful to Dr A. Ahond and Dr C. Poupat for this personal communication.
23. (a) A. G. Chaudhary, J. M. Rimoldi and D. G. I. Kingston, J. Org. Chem., 1993, 58, 3798;
24. (b) S.-H. Chen, S. Huang, J. Kant, C. Fairchild, J. Wei and V. Farina, J. Org. Chem., 1993, 58, 5028;
25. (c) V. Farina, S.-H. Chen, D. R. Langley, M. D. Wittman, J. Kant and D. Vyas, Eur. Pat. Appl. EP 590 267, 6 Apr. 1994 (Chem. Abstr., 1994, 121, 205747n).
26. (a) L. Ettouati, A. Ahond, C. Poupat and P. Potier, Tetrahedron, 1991, 47, 9823;
27. (b) P. H. G. Wiegerinck, L. Fluks, J. B. Hammink, S. J. E. Mulders, F. M. H. de Groot, H. L. M. van Rosendaal and H. W. Sheeren, J. Org. Chem., 1996, 61, 7092;
28. (c) I. Fenoglio, G. M. Nano, D. G. V. Velde and G. Appendino, Tetrahedron Lett., 1996, 37, 3203;
29. (d) H. Poujol, A. A. Mourabit, A. Ahond, C. Poupat and P. Potier, Tetrahedron, 1997, 53, 12575, and references cited therein.
30. While this work was in progress, the first semisynthesis of 7-deoxybaccatin from 3 was reported, in 15 steps, and 1.7% overall yield (ref. 10d).
31. R. Matović and R. N. Saičić, Chem. Commun., 1998, 1745.
32. G. Appendino, P. Gariboldi, A. Pisetta, E. Bombardelli and B. Gabetta, Phytochemistry, 1992, 31, 4253.
33. J.-N. Denis, A. Correa and A. E. Greene, J. Org. Chem., 1990, 55, 1957.
34. K. C. Nicolaou, P. G. Nantermet, H. Ueno, R. K. Guy, A. Couladouros and E. J. Sorensen, J. Am. Chem. Soc., 1995, 117, 624.
35. A. M. Kanazawa, J.-N. Denis and A. E. Greene, J. Chem. Soc., Chem. Commun., 1994, 2591.
36. D. B. Dess and J. C. Martin, J. Org. Chem., 1983, 48, 4155.
37. A. Bowers, T. G. Halsall, E. R. H. Jones and A. J. Lemin, J. Chem. Soc., 1953, 2548.
38. N. F. Magri, D. G. I. Kingston, C. Jitrangsri and T. Piccariello, J. Org. Chem., 1986, 51, 3239.