Diastereoselective synthesis of (1S,2S,3R,4R) and (1R,2S,3R,4S) -bicyclo[2.2.1]hept-2-amino-2,3-dicarboxylic acids: New conformationally-constrained (S)-aspartic acid analogues

Tetrahedron Asymmetry

Volumn 7, Issue 5, 1996, Pages 1521-1528

  Buñuel, Elena ^a   Cativiela, Carlos ^a   Diaz De Villegas, Maria D ^a  

^a UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO BICYCLO[2.2.1]HEPTANE 2,3 DICARBOXYLIC ACID; AMINO ACID; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029890686     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00172-3     Document Type: Article

References (30)

1. (a) Watkins, J.C.; Olverman, H. J.; "Excitatory Amino Acids in Health and Disease", Lodge, D., Ed. John Wiley and Sons, Chichester, England, 1988.
2. (b) Simon, R. P. Ed.; "Excitatory Amino Acids", Thieme, New York, 1992.
3. (c) Dingledine, R.; Mc Bain, C. J.; Mc Namara, J. O.; Trends. Pharmacol. Sci., 1990, 11, 334.
4. (d) Mc Culloch, J.; Br. J. Clin. Pharmacol., 1992, 34, 106.
5. (e) Lipton, S. A.; Rosenberg, P. A.; New Engl. J. Med., 1994, 330, 613.
6. (a) Collingidge, G. L.; Watkins, J. C., Eds., "The NMDA Receptor", IRL Press at Oxford University Press, Oxford, England, 1994.
7. (b) Krogsgaard-Larsen, P.; Hansen, J. J., Eds., "Excitatory Amino Acid Receptors: Design of Agonists and Antagonists". Ellis. Horwood: Chichester, England, 1992.
8. (a) Watkins, J. C.; Olverman, H. J.; Trends Neurosci., 1987, 10, 265.
9. (b) Bigge, C. F.; Biochem. Pharmacol., 1993, 45, 1547.
10. o 50, Tetrahedron, 1993, 49, 3433.
11. (b) Giannis, A.; Kolter, T.;Angew. Chem. Int Ed. Engl., 1993, 32, 1244.
12. (c) Gante, J.; Angew. Chem. Int. Ed. Engl., 1994, 33, 1720.
13. (d) Liskamp, R. M. J., Rec. Trav. Chim. Pays-Bas, 1994, 113, 1.
14. See for example: (a) Kazmierski, W.; Hruby, V. J.; Tetrahedron, 1988, 44, 697.
15. (b) Kazmierski, W.; Wire, W. S.; Lui, G. K.; Knapp, R. J.; Shook, J. E.; Burks, T. F.; Yamamuran, H. I.; Hruby, V. J.; J. Med. Chem., 1988, 31, 2170.
16. (c) Hsieh, K. H.; LaHann, T. R.; Speth, R. C.; J. Med. Chem., 1989, 32, 898.
17. (d) Holladay, M. W.; Lin, C. W.; May, C. S.; Garvey, D. S.; Witte, D. G.; Miller, T. R.; Wolfram, C. A. W.; Nadzan, A. M.; J. Med. Chem., 1991, 34, 455.
18. (e) Schiller, P. W.; Weltrowska, G.; Nguyen, T. M. D.; Lamieux, C.; Chung, N. N.; Marsden, B. J.; Wilkes, B. C.; J. Med. Chem., 1989, 32,3125.
19. See for example: (a) "Amino Acids, Peptides and Proteins". The Chemical Society: Cambridge, 1968-1991; Vois 1-22.
20. (b) Barret, G. C. Ed.; "Chemistry and Biochemistry of the Amino Acids", Chapman and Hall. London 1985.
21. (c) O'Donnell, M. J. Ed. "α-Amino Acid Synthesis " Tetrahedron Symposia-in-print 1988, 44, 5253.
22. (d) Williams, R. M. "Synthesis of Optically Active α-Amino Acids " Pergamon Press: Oxford 1989.
23. (e) Duthaler, R. O.; Tetrahedron, 1994, 50, 1539.
24. See for example: (a) Veber, D. F.; Freidinger, R. M.; Trends Neurosci.,1995, 392.
25. (b) Mendel, D.; Ellman, J. A.; Chang, Z.; Veenstra, D. L.; Kollman, P. A.; Schultz, P. G.; Nature, 1992, 256, 1798.
26. (c) Zhu, Y. F.; Yamazaki, T.; Tsang, J. W.; Lok, A.; Goodman, M.; J. Org. Chem.; 1992, 57, 1074.
27. (d) Mendel, D.; Ellman, J. ; Schultz, P. G.; J. Am. Chem. Soc., 1993, 115, 4359.
28. (a) Buñuel, E.; Cativiela, C.; Diaz-de-Villegas, M. D.; Tetrahedron: Asymmetry, 1994, 5, 157.
29. (b) Buñuel, E.; Cativiela, C.; Diaz-de-Villegas, M. D.; Garcia, J. I.; Tetrahedron: Asymmetry, 1994, 5, 759.
30. See for example: Avenoza, A.; Cativiela, C.; Mayoral, J. A.; Roy, M. A.; Tetrahedron, 1989, 45, 3923.