A new enantiocontrolled route to (-)-kainic acid

Heterocycles

Volumn 44, Issue 1, 1997, Pages 129-132

  Kawamura, Mitsuhiro ^a   Ogasawara, Kunio ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000002193     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-96-s38     Document Type: Article

References (26)

1. Pertinent reviews, see: K. Hashimoto and H. Shirahama, J. Syn. Org. Chem. Jpn., 1989, 47, 212;
2. K. Hashimoto and H. Shirahama, idem, Trends in Organic Chemistry, 1991, 2, 1.
3. R. M. Williams, 'Synthesis of Optically Active α-Amino Acids,' Pergamon Press, 1989.
4. Enantiocontrolled syntheses of (-)-kainic acid: a) W. Oppolzer and K. Thirring, J. Am. Chem. Soc., 1982, 104, 4978.
5. b) J. E. Baldwin and C. -S. Li, J. Chem. Soc., Chem. Commun., 1987, 166;
6. J. E. Baldwin, M. G. Moloney, and A. F. Parsons, Tetrahedron, 1990, 46, 7263.
7. c) J. Cooper, D. W. Knight, and P. T. Gallagher, J. Chem. Soc., Chem. Commun., 1987, 1220;
8. J. Cooper, D. W. Knight, and P. T. Gallagher, idem, J. Chem. Soc., Perkin Trans. 1, 1992, 553.
9. d) S. Takano, Y. Iwabuchi, and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1988, 1204.
10. e) S. Takano, T. Sugihara, S. Satoh, and K. Ogasawara, J. Am. Chem. Soc., 1988, 110, 6467.
11. f) A. Barco, S. Benetti, G. P. Pollini, G. Spalluto, and V. Zanirato, J. Chem. Soc., Chem. Commun., 1991, 390.
12. g) S. Takano, K. Inomata, and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1992, 169.
13. h) S. Hatakeyama, K. Sugawara, and S. Takano, J. Chem. Soc., Chem. Commun., 1993, 125.
14. i) S. -e. Yoo, S. -H. Lee, N. Jeong, and I. Cho, Tetrahedron Lett., 1993, 34, 3435;
15. S. -e. Yoo and S. H. Lee, J. Org. Chem., 1994, 59, 6968.
16. (+)-Norcamphor (>95% ee) was prepared from (+)-endo-norborneol kindly supplied by Chisso Corporation.
17. Some precedented enantiocontrolled syntheses of natural products using (+)-norcamphor as the starting material: a) M. Kawamura and K. Ogasawara, Tetrahedron Lett., 1995, 36, 3369.
18. b) M. Saito, M. Kawamura, and K. Ogasawara, Tetrahedron Lett., 1995, 36, 9003.
19. c) M. Kawamura and K. Ogasawara, J. Chem. Soc., Chem. Commun., 1995, 2403.
20. A pertinent review, see: S. Takano and K. Ogasawara, J. Syn. Org. Chem. Jpn., 1977, 35, 795.
21. 3) (>99% ee, CHIRALCEL OD, 10% i-PrOH-hexane).
22. a) O. Mitsunobu, Synthesis, 1981, 1.
23. b) D. L. Hughes, Org. Reactions, 1992, 42, 335.
24. M. S. Motawia, J. Wengel, A. E. -S. Abdel-Megid, and E. B. Pedersen, Synthesis, 1989, 384.
25. J. A. Marshall and D. E. Seitz, J. Org. Chem., 1974, 39, 1814.
26. S. Yamada, D. Morizono, and K. Yamamoto, Tetrahedron Lett., 1992, 33, 4329.