Studies directed toward the synthesis of taxanes: Evaluation of the B- ring formation by an intramolecular nitrile oxide cycloaddition

European Journal of Organic Chemistry

Volumn , Issue 12, 1999, Pages 3241-3249

  Nivlet, Alex ^a   Dechoux, Luc ^a   Martel, Jean Philippe ^a   Proess, Gottfried ^a   Mannes, Dietrich ^a   Alcaraz, Lilian ^b   Harnett, Jerry J ^b   Le Gall, Thierry ^a   Mioskowski, Charles ^a,b  

^a CEA SACLAY   (France)

^b UNIVERSITÉ DE STRASBOURG   (France)

Author keywords

Cycloaddition reactions; Isoxazoline; Macrocycles; Nitrile oxide; Taxol

Indexed keywords

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ORGANIC CHEMISTRY; SYNTHESIS;

EID: 0032726377     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-0690(199912)1999:12<3241::AID-EJOC3241>3.0.CO;2-9     Document Type: Article

References (21)

1. Reported total syntheses of taxol: [1a] 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, J. H. Liu, J. Am. Chem. Soc. 1994, 116, 1599-1600.
2. [1b] 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.
3. [1c] J. J. Masters, J. T. Link, L. B. Snyder, W. B. Young, S. J. Danishefsky, Angew. Chem. Int. Ed. Engl. 1995, 34, 1723-1726.
4. [1d] 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. L. McGrane, W. Meng, M. G. Natchus, A. J. Shuker, J. C. Sutton, R. E. Taylor, J. Am. Chem. Soc. 1997, 119, 2757-2758.
5. [1e] T. Mukaiyama, I. Shiina, H. Iwadare, H. Sakoh, Y. Tani, M. Hasegawa, K. Saitoh, Proc. Japan Acad. 1997, 73(B), 95-100.
6. [1f] K. Morihira, R. Hara, S. Kawahara, T. Nishimori, N. Nakamura, H. Kusama, I. Kuwajima, J. Am. Chem. Soc. 1998, 120, 12980-12981.
7. L. Alcaraz, J. J. Harnett, C. Mioskowski, T. Le Gall, D.-S. Shin, J. R. Falck, J. Org. Chem. 1995, 60, 7209-7214.
8. Review on the synthesis of carbocyclic eight-membered rings: N. A. Petasis, M. A. Patane, Tetrahedron 1992, 48, 5757-5821.
9. Review on intramolecular 1,3-dipolar cycloadditions: P. A. Wade in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press, 1991, Vol. 4, pp. 1111-1168.
10. Y. Queneau, W. J. Krol, W. G. Bornmann, S. J. Danishefsky, J. Org. Chem. 1992, 57, 4043-4047.
11. Z. Wang, S. E. Warder, H. Perrier, E. L. Grimm, M. A. Bernstein, R. G. Ball, J. Org. Chem. 1993, 58, 2931-2932.
12. J. P. McCormick, D. L. Barton, J. Org. Chem. 1980, 45, 2566-2570.
13. T. Imamoto, N. Takiyama, K. Nakamura, T. Hatajima, Y. Kamiya, J. Am. Chem. Soc., 1989, 111, 4392-4398.
14. P. J. Garegg, B. Samuelsson, J. Chem. Soc., Chem. Commun. 1979, 978-980.
15. G. A. Lee, Synthesis 1982, 508-509.
16. T. Mukaiyama, T. Hoshino, J. Am. Chem. Soc. 1960, 82, 5339-5342.
17. S. Nunomoto, Y. Kawakami, Y. Yamashita, J. Org. Chem. 1983, 48, 1912-1914.
18. D. A. Evans, L. K. Truesdale, G. L. Carroll, J. Chem. Soc., Chem. Commun. 1973, 55-56.
19. For other stable aliphatic nitrile oxides, see: A. P. Kozikowski, X.-M. Cheng, Tetrahedron Lett. 1987, 28, 3189-3192, and references cited therein.
20. The formation of the A/B ring system by the intramolecular cyclisation of an aromatic nitrile oxide (a Friedel-Crafts reaction rather than a [3 + 2] cycloaddition) was recently reported: Y. Hirai, H. Nagaoka, Tetrahedron Lett. 1997, 38, 1969-1970. For a related approach see also: P. Magnus, N. Westwood, M. Spyvee, C. Frost, P. Linnane, F. Tavares, V. Lynch, Tetrahedron 1999, 55, 6435-6452.
21. The formation of the A/B ring system by the intramolecular cyclisation of an aromatic nitrile oxide (a Friedel-Crafts reaction rather than a [3 + 2] cycloaddition) was recently reported: Y. Hirai, H. Nagaoka, Tetrahedron Lett. 1997, 38, 1969-1970. For a related approach see also: P. Magnus, N. Westwood, M. Spyvee, C. Frost, P. Linnane, F. Tavares, V. Lynch, Tetrahedron 1999, 55, 6435-6452.