Synthesis of 2-fluoro analog of 6-aminonorbornane-2,6-dicarboxylic acid: A conformationally rigid glutamic acid derivative

Tetrahedron

Volumn 55, Issue 44, 1999, Pages 12741-12750

  Ito, Hisanaka ^a   Saito, Akio ^a   Kakuuchi, Akito ^a   Taguchi, Takeo ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

6 AMINONORBORNANE 2,6 DICARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; GLUTAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CHEMICAL BOND; DEPOLARIZATION; DIASTEREOISOMER; DRUG CONFORMATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; ENANTIOMER; NEUROPHARMACOLOGY; NEWBORN; NONHUMAN; OPTICAL ROTATION; PRIORITY JOURNAL; RAT; REACTION ANALYSIS; SPINAL CORD; STEREOCHEMISTRY;

ANIMALIA;

EID: 0033615752     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00785-1     Document Type: Article

References (32)

1. a) Hayashi, Y.; Tanabe, Y.; Aramori, I.; Masu, M.; Shimamoto, K.; Ohfune, Y.; Nakanishi, S. J. Pharmacol. 1992, 107, 539.
2. b) Ohfune, Y.; Shimamoto, K.; Ishida, M.; Shinozaki, H. Bioorg. Med. Chem. Lett. 1993, 3, 15.
3. c) Ishida, M.; Saitoh, T.; Nakamura, Y.; Kataoka, K.; Shinozaki, H. Eur. J. Pharmacol. 1994, 268, 267.
4. a) Schoepp, D. D.; Johnson, B. G.; Monn, J. A. J. Neurochem. 1992, 58, 1184.
5. b) Monn, J. A.; Valli, M. J.; Johnson, B. G.; Salhoff, C. R.; Wright, R. A.; Howe, T.; Bond, A.; Lodge, D.; Griffy, K.; Tizzano, J. P.; Schoepp, D. D. J. Med. Chem. 1996, 39, 2990.
6. c) Monn, J. A.; Valli, M. J.; Massey, S. M.; Wright, R. A.; Salhoff, C. R.; Johnson, B. G.; Howe, T.; Alt, A.; Rhodes, G. A.; Robey, R. L.; Griffy, K. R.; Tizzano, J. P.; Kallmann, M. J.; Helton, D. R.; Schoepp, D. D. J. Med. Chem. 1997, 40, 528.
7. Kozikowski, A. P.; Steensma, Darryl.; Alaldi, G. L.; Tuckmantel, W.; Wang, S.; Pshenichkin, E.; Wroblewski, J. T. J. Med. Chem. 1998, 41, 1641 and references cited.
8. a) Davies, J.; Francis, A. A.; Jones, A. W.; Watkins, J. C. Neurosci. Lett. 1981, 21, 77.
9. b) Nakajima, Y.; Iwakabe, H.; Akazawa, C.; Nawa, H.; Shigemoto, R.; Mizuno, N.; Nakanishi, S. J. Biol. Chem. 1993, 268, 11868.
10. c) Flor, P.; Lukic, S.; Ruegg, D.; Leonhardt, T,; Knopfef, T.; Kuhn, R. Neuropharmacology 1995, 34, 149.
11. d) Jane, D. E.; Pittaway, K.; Sunter, D. C.; Thomas, N. K.; Watkins, J. C. Neuropharmacology 1995, 34, 851.
12. e) Roberts, P. J. Neuropharmacology 1995, 34, 813.
13. a) Saitoh, T.; Ishida, M.; Shinozaki, H. Br. J. Pharmacol. 1998, 123, 771.
14. b) Shibuya, A.; Sato, A.; Taguchi, T. Bioorg. Med. Chem. Lett. 1998, 8, 1979.
15. Ito, H.; Saito, A.; Taguchi, T. Tetrahedron Asym. 1998, 9, 1979.
16. Ito, H.; Saito, A.; Taguchi, T. Tetrahedron Asym. 1998, 9, 1989.
17. Regioselection in hydroboration due to the inductive effect of C-2 substituent on bicyclo[2.2.1]hept-5- ene derivatives: a) Fischer, W.; Grob, C. A.; von Sprecher, G. Helv. Chim. Acta 1980, 63, 806.
18. b) Glass, R. S.; Sabahi, M.; Singh, W. P. J. Org. Chem. 1992, 57, 2683.
19. Examples of electronic directing substituent effect in hydroboration: a) Brown, H. C.; Knights, E. F. J. Am. Chem. Soc. 1968, 90, 4439.
20. b) Pasto, D. J.; Hickman, J. ibid. 1968, 90, 4445.
21. c) Ng, F.; Chiu, P.; Danishefsky, S. J. Tetrahedron Lett. 1998, 39, 767.
22. Regiochemistry and exo-attack in hydroboration reaction of 2 was confirmed by X-ray analysis of p- nitrobenzoate of (±)-6.
23. Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4156.
24. Examples of the Strecker and the Bucherer reactions of norbornane derivatives: a) Tager, H. S.; Christensen, H. N. J. Am. Chem. Soc. 1972, 94, 968.
25. b) Layton, W. J.; Smith, S. L.; Crooks, P. A.; Deeks, T.; Waigh, R. D. J. Chem. Soc. Perkin Trans. 1. 1984, 1283.
26. c) G. Cativiela, C.; Lopez, P.; Mayoral, J. A. Tetrahedron: Asymmetry, 1990, 1, 379.
27. d) Bolch, R.; Brillet-Fernandez, C.; Mandvulle, Tetrahedron: Asymmetry, 1994, 5, 745.
28. e) Bunuel, E.; Cativiela, C.; Daiz-de-Villegas, M. D. Tetrahedron: Asymmetry, 1996, 7, 1521.
29. f) Teiller, F.; Acher, F.; Brabet, I.; Pin, J.-P.; Azerad, R. Bioorg. Med. Chem. 1998, 6, 195.
30. Jennings, W. B.; Lovely, C. J. Tetrahedron 1991, 47, 5561.
31. 2 AlCN instead of TMSCN was not effective.
32. Shinozaki, H.; Ishida, M.; Shimamoto, K.; Ohfune, Y. Br. J. Pharmacol. 1989, 98, 1213.