Novel synthetic strategy towards taxol by macrocyclization reaction - Conformational requirement of ring A

European Journal of Organic Chemistry

Volumn , Issue 16, 2006, Pages 3681-3686

  Canesi, Sylvain ^a   Berthiaume, Gilles ^a   Deslongchamps, Pierre ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

Carvone; Conformation; Epimer; Macrocyclization; Taxane

Indexed keywords

EID: 33748359674     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600284     Document Type: Article

References (27)

1. a) A. Toro, P. Nowak, P. Deslongchamps, J. Am. Chem. Soc. 2000, 122, 4526-4527;
2. b) J. Germain, P. Deslongchamps, J. Org. Chem. 2002, 67, 5269-5278;
3. c) A. Toro, P. Deslongchamps, J. Org. Chem. 2003, 68, 6847-6858;
4. d) P. Soucy, A. L'Heureux, A. Toro, P. Deslongchamps, J. Org. Chem. 2003, 68, 9983-9987;
5. e) review: E. Marsault, A. Toro, P. Nowak, P. Deslongchamps, Tetrahedron 2001, 57, 4243-4260.
6. a) 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, E. J. Sorensen, Nature 1994, 367, 630-634;
7. b) R. A. Holton, C. Somoza, H. B. Kim, 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. Hang, K. K. Murthi, L. N. Gentile, J. H. Liu, J. Am. Chem. Soc. 1994, 116, 1597-1598;
8. c) J. J. Masters, J. T. Link, L. B. Snyder, W. B. Young, S. J. Danishefsky, Angew. Chem. Int. Ed. Engl. 1995, 34, 1723-1726;
9. d) P. A. Wender, N. F. Badham, S. P. Conway, P. E. Floreansic, T. E. Glass, J. B. Houze, N. E. Krauss, D. Lee, D. J. Marquess, P. L. McGrane, W. Meng, M. G. Natchus, A. J. Shuker, J. C. Sutton, R. E. Taylor, J. Am. Chem. Soc. 1997, 119, 2757-2758;
10. e) T. Mukaiyama, I. Shiina, H. Iwadare, H. Sakoh, Y. Tani, M. Hasegawa, K. Saitoh, Proc. Jpn. Acad. Ser. B 1997, 73, 95-100;
11. f) K. Morihara, R. Hara, S. Kawahara, T. Nishimori, N. Nakamura, H. Kusama, I. Kuwajima, J. Am. Chem. Soc. 1998, 120, 12980-12981.
12. a) A. Srikrishna, T. J. Reddy, K. P. Praveen, Chem. Commun. 1996, 1369-1370;
13. b) A. Srikrishna, T. J. Reddy, K. P. Praveen, J. Chem. Soc., Parkin Trans. 1 1998, 3143-3144;
14. c) G. Mehta, S. K. Chattopadhyay, J. D. Umarye, Tetrahedron Lett. 1999, 40, 4881-4884.
15. Epoxidation of (-)-(R)-Carvone followed by Birch reduction and methylation of the resulting enolate gave 4 in 60% overall yield: J. D. McChesney, T. N. Thompson, J. Org. Chem. 1985, 50, 3473-3481.
16. S. L. Schreiber, J. Am. Chem. Soc. 1980, 102, 6163-6165.
17. B. Boulin, B. Arreguy-San Miguel, B. Delmond, Tetrahedron 2000, 56, 3927-3932.
18. 13 in 17 is axial [δ = 5.32 (dd, J = 9.4, 6.8 Hz, 1 H) ppm] as in compound 18′ [δ = 4.18 (dd, J = 12.2, 9.2 Hz, 1 H) ppm].
19. F. Munyemana, A. M. Frisque-Hesbain, A. Devos, L. Ghosez, Tetrahedron Lett. 1989, 30, 3077-3080.
20. We tried with palladium to generate the π-allyl complex in order to form the macrocycle, but to our disapointment this methodology failed.
21. Several studies have been undertaken to prepare Taxol from an intermolecular reaction starting from a polyfunctionalized ring A. Much work has failed, just few examples have given some useful results and only when a simpler ring A precursor was used: a) Y. Lu Fung, A. G. Fallis, Tetrahedron Lett. 1993, 34, 3367-3370;
22. b) D. Crich, S. Natarajan, J. Chem. Soc., Chem. Commun. 1995, 1, 85-86;
23. c) Y. F. Lu, C. W. Harwig, A. G. Fallis, Can. J. Chem. 1995, 73, 2253-2262;
24. d) C. W. Harwig, S. Py, A. G. Fallis, J. Org. Chem. 2001, 66, 4170-4179;
25. e) J. D. Winkler, S. K. Bhattacharya, R. A. Batey, Tetrahedron Lett. 1996, 37, 8069-8072;
26. f) G. Chouraqui, M. Petit, P. Phansavath, C. Aubert, M. Malacria, Eur. J. Org. Chem. 2006, 6, 1413-1421.
27. 13.