An efficient synthesis of new diastereomeric enantiopure 1-aminocyclopentane-1,2,4-tricarboxylic acids

Tetrahedron Asymmetry

Volumn 17, Issue 9, 2006, Pages 1430-1436

  Caputo, Francesco ^a   Clerici, Francesca ^a   Gelmi, Maria Luisa ^a   Pellegrino, Sara ^a   Pocar, Donato ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1 AMINOCYCLOPENTANE 1,2,4 TRICARBOXYLIC ACID; CARBONYL DERIVATIVE; CARBOXYL GROUP; CARBOXYLIC ACID DERIVATIVE; GLUTAMIC ACID; NORBORNENE DERIVATIVE; TRICARBOXYLIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CYCLOADDITION; DIASTEREOISOMER; DIELS ALDER REACTION; ENANTIOMER; OXIDATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

EID: 33746842672     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.05.001     Document Type: Article

References (39)

1. Curry K., Peet M.J., Magnuson D.S.K., and McLennan H. J. Med. Chem. 31 (1988) 864-867
2. Ezquerra J., Yruretagoyena B., Avendano C., de la Cuesta E., Gonzales R., Prieto L., Pedregal C., Espada M., and Prowse W. Tetrahedron 51 (1995) 3271-3278
3. Tellier F.J., Acher F.C., Brabet I.N., Pin J.-P., Bockaert J., and Azerad R. Biorg. Med. Chem. Lett. 5 (1995) 2627-2632
4. Acher F.C., Tellier F.J., Azerad R., Brabet I.N., Fagni L., and Pin J.-P.R. J. Med. Chem. 40 (1997) 3119-3129
5. Ma D., Ma J., and Dai L. Tetrahedron: Asymmetry 8 (1997) 825-827
6. Kozikowski A.P., Steensma D., Araldi G.L., Tuckmantel W., Wang S., Pshenichkin S., Surina E., and Wroblewski J.T. J. Med. Chem. 41 (1998) 1641-1650
7. Pellicciari R., Marinozzi M., Costantino G., Natalini B., Moroni F., and Pellegrini D. J. Med. Chem. 42 (1999) 2716-2720
8. Bradley D.M., Mapitse R., Thomson N.M., and Hayes C.J. J. Org. Chem. 67 (2002) 7613-7617
9. Battistini L., Curti C., Zanardi F., Rassu G., Auzzas L., and Casiraghi G. J. Org. Chem. 69 (2004) 2611-2613
10. Baudy R.B., Sze J.Y., and Butera J.A. Synth. Commun. 34 (2004) 3949-3954
11. Ung A.T., Pyne S.G., Batenburg-Nguyen U., Davis A.S., Sherif A., Bischoff F., and Lesage A.S.J. Tetrahedron 61 (2005) 1803-1812
12. Choi D.W. J. Neurosci. 1 (1988) 623-634
13. Choi D.W. J. Neurosci. 10 (1990) 2493-2501
14. In: Wheal H.V., and Thomson A.M. (Eds). Excitatory Amino Acids and Synaptic Transmissions (1995), Academic Press, London
15. Ozawa S., Kamiya H., and Tsuzuki K. Prog. Neurobiol. 54 (1998) 581-618
16. Braüner-Osborne H., Egebjerg J., Nielsen E.Ø., Madsen U., and Krogsgaard-Larsen P. J. Med. Chem. 43 (2000) 2609-2645
17. Lee H., Zhu X., O'Neill M., Webber K., Casadesus G., Marlatt M., Raina A.K., Perry G., and Smith M.A. Acta Neurobiol. Exp. 64 (2004) 89-98
18. Ornstein P.L., Schoepp D.D., and Monn J.A. Curr. Pharm. Des. 1 (1995) 355
19. Jullian N., Brabet I., Pin J.-P., and Acher F.C. J. Med. Chem. 42 (1999) 1546-1555
20. Bertrand H.-O., Bessis A.-S., Pin J.-P., and Acher F.C. J. Med. Chem. 45 (2002) 3171-3183
21. Nakasihi S. Sciences 258 (1992) 597-603
22. Hollmann M., and Heinemann S. Annu. Rev. Neurosci. 17 (1994) 31-108
23. Knopfel T., Kuhn R., and Allgeier H. J. Med. Chem. 38 (1995) 1417-1426
24. Conn P.J., and Pin J.P. Annu. Rev. Pharmacol. Toxicol. 37 (1997) 205-237
25. Palmer E., Monaghan D.T., and Cotman C.W. Eur. J. Pharmacol. 166 (1989) 585-587
26. Joly C., Gomeza J., Brabet I., Curry K., Bockaert J., and Pin J.-P. J. Neurosci. 15 (1995) 3970-3981
27. Monn J.A., Valli M.J., Massey S.M., Wright R.A., Salhoff C.R., Johnson B.G., Howe T., Alt C.A., Rhodes G.A., Robey R.L., Griffey K.R., Tizzano J.P., Kallman M.J., and Helton D. J. Med. Chem. 40 (1997) 528-537
28. Clerici F., Gelmi M.L., and Pocar D. J. Org. Chem. 64 (1999) 726-730
29. Clerici F., Gambini A., and Gelmi M.L. J. Org. Chem. 64 (1999) 5764-6767
30. Clerici F., Gambini A., and Gelmi M.L. J. Org. Chem. 65 (2000) 6138-6141
31. Clerici F., Gambini A., and Gelmi M.L. J. Org. Chem. 65 (2001) 4941-4944
32. Abbiati G., Clerici F., Gambini A., Gelmi M.L., and Pilati T. J. Org. Chem. 65 (2001) 6299-6304
33. Clerici F., Gambini A., Gelmi M.L., and Nava D. Tetrahedron 57 (2001) 6429-6438
34. Clerici F., Gambini A., Gelmi M.L., and Pilati T. Tetrahedron: Asymmetry 12 (2001) 2663-2669
35. Caputo F., Clerici F., Gelmi M.L., Nava D., and Pellegrino S. Tetrahedron 62 (2006) 1288-1294
36. Cativiela C., Diaz de Villegas M.D., and Galvez J.A. Synthesis 25 (1990) 198-199
37. Cativiela C., Loper P., and Mayoral J.A. Tetrahedron: Asymmetry 6 (1991) 449-456
38. Cativiela C., Loper P., and Mayoral J.A. Tetrahedron: Asymmetry 1 (1990) 379-388
39. Caputo F., Clerici F., Gelmi M.L., Pellegrino S., and Pilati T. Tetrahedron: Asymmetry 17 (2006) 61-67