The stereoselective preparation of substituted pyrrolidines using titanium- And zirconium-mediated diene metallabicyclisation methodology: The total synthesis of (-)-α-kainic acid

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 19, 2000, Pages 3194-3204

  Campbell, Andrew D ^a   Raynham, Tony M ^b   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b ROCHE PRODUCTS LTD   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANIC ACIDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); TITANIUM; ZIRCONIUM;

METALLABICYCLISATION;

AROMATIC COMPOUNDS;

EID: 0034619268     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/b005853j     Document Type: Article

References (45)

1. For reviews see: A. F. Parsons, Tetrahedron, 1996, 52, 4149;
2. M. G. Moloney, Nat. Prod. Rep., 1998, 205.
3. S. Murakami, T. Takemoto, Z. Shimizu and K. Daigo, Yakugaku Kenkyu, 1973, 25, 571.
4. G. Impellizzeri, S. Mangiafico, G. Oriente, M. Piatelli, S. Sciuto, E. Fattorusso, S. Magno, S. Santacroce and D. Sica, Phytochemistry, 1975, 14, 1549.
5. G. Balansard, M. Pellegrini, C. Cavilli and P. Timon-David, Ann. Pharm. Fr., 1983, 41, 77.
6. M. Sakai, Takeda Kenkhyusho Neinpo, 1960, 19, 27.
7. S. Marahami, T. Takemoto and N. Shimiza, Jap. Pat., 4947, 1954
8. (Chem. Abstr., 1955, 49, 13604i).
9. K. Daigo, Yakugaku Zasshi, 1959, 79, 350.
10. K. Konno, H. Shirahama and T. Matsumoto, Tetrahedron Lett., 1983, 24, 939.
11. K. Konno, K. Hashimoto, Y. Ohfune, H. Shirahama and T. Matsumoto, J. Am. Chem. Soc., 1988, 110, 4807.
12. For recent syntheses of kainic acid see: J. Clayden and K. Tchabanenko, Chem. Commun., 2000, 317;
13. M. V. Chevliakov and J. Montgomery, J. Am. Chem. Soc., 1999, 121, 11139;
14. J. Cossy, M. Cases and D. G. Pardo, Synlett, 1998, 507;
15. I. Collado, J. Ezquerra, A. I. Mateo and A. Rubio, J. Org. Chem., 1998, 63, 1995;
16. M. Kawamura and K. Ogasawara, Heterocycles, 1997,44,129.
17. A. F. Parsons and R. J. K. Taylor, J. Chem. Soc., Chem. Commun., 1994, 1945.
18. A. Bird, R. J. K. Taylor and X. Wei, Synlett, 1995, 1237.
19. E. Negishi, F. E. Cederbaum and T. Takahashi, Tetrahedron Lett., 1986, 27, 2829;
20. E. Negishi and T. Takahashi, Acc. Chem. Res., 1994, 27, 124.
21. S. E. Yoo, S. H. Lee, N. Jeong and I. Cho, Tetrahedron Lett., 1993, 34, 3435;
22. O. Miyata, Y. Ozawa, I. Ninomiya and T. Naito, Synlett, 1997, 275;
23. M.-P. Bertrand, S. Gastaldi and R. Nourguier, Tetrahedron Lett., 1996, 37, 1229;
24. See also M. D. Bachi and A. Melman, J. Org. Chem., 1997, 62, 1896.
25. T. Takahashi, D. Y. Kondakov and N. Suzuki, Organometallics, 1994, 13, 3411.
26. (a) Y. Takayama, Y. Gao and F. Sato, Angew. Chem., Int. Ed. Engl., 1997, 36, 851;
27. (b) Y. Takayama, S. Okamoto and F. Sato, Tetrahedron Lett., 1997, 38, 8351;
28. Y. Takayama, S. Okamoto and F. Sato, J. Am. Chem. Soc., 1999, 121, 3559;
29. F. Sato, H. Urabe and S. Okamoto, Synlett, 2000, 753.
30. Preliminary communication: A. D. Campbell, T. M. Raynham and R. J. K. Taylor, Chem. Commun., 1999, 245.
31. J. Barluenga, R.-M. Canteli and J. Fiórez, J. Org. Chem., 1994, 59, 602.
32. J. M. Davis, R. J. Whitby and A. Jaxa-Chamiec, Tetrahedron Lett., 1992, 33, 5655.
33. D. F. Taber, J. P. Louey, Y. Wane, W. A. Nugent, D. A. Dixon and R. L. Harlow, J. Am. Chem. Soc., 1994, 116, 9457.
34. (a) A. D. Campbell, T. M. Raynham and R. J. K. Taylor, Synthesis, 1998, 1707;
35. (b) A. McKillop, R. J. K. Taylor, R. J. Watson and N. Lewis, Synthesis, 1994, 31 and references therein.
36. A. Barco, S. Benetti and G. Spalluto, J. Org. Chem., 1992, 57, 6279.
37. W. Oppolzer and K. Thirring, J. Am. Chem. Soc., 1982, 104, 4978.
38. (a) A. Rubio, J. Ezquerra, A. Escribano, M. J. Rumuiñán and J. J. Vaquero, Tetrahedron Lett., 1998, 39, 2171;
39. (b) H. Maeda and G. A. Kraus, J. Org. Chem., 1997, 62, 2314.
40. Z.-Y. Wei and E. Knaus, Synthesis, 1994, 1463.
41. J. F. Collins, A. J. Dixon, G. Badman, G. De Sarro, A. G. Chapman, G. P. Hart and B. S. Meldrum, Neurosci. Lett., 1984, 51, 371.
42. S. Takano, K. Inomata and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1992, 169.
43. M. P. Crozet, M. Kaafarani and J. M. Surzur, Bull. Soc. Chim. Fr., 1984, 11-390.
44. B. W. Horrom and H. E. Zaugg, J. Am. Chem. Soc., 1956, 79, 1754.
45. S. Hanessian and S. Ninkovic, J. Org. Chem., 1996, 61, 5418.