Synthesis of a constrained enkephalin analog to illustrate a novel route to the piperazinone ring structure

Tetrahedron Letters

Volumn 39, Issue 3-4, 1998, Pages 221-224

  Shreder, Kevin ^a   Zhang, Li ^a   Goodman, Murray ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENKEPHALIN DERIVATIVE; FUNCTIONAL GROUP; PIPERAZINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; PRECURSOR; REACTION ANALYSIS;

EID: 0032518653     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10530-5     Document Type: Article

References (25)

1. 1. (a) Pohlmann, V.; Schanen, V.; Guillaume, D.; Quirion, J.-C.; Husson, H.-P., J. Org. Chem. 1997, 62, 1016-1022.
2. (b) Bhatt, U.; Mohamed, N.; Just, G. Tetrahedron Let. 1997, 38, 3679-3682.
3. (c) Kolter, T.; Dahl, C.; Giannis, A. Liebigs Ann. 1995, 625-629.
4. (d) DiMaio, J.; Belleau, B. J. Chem. Soc. Perk. Trans. I 1989, 1687-1689.
5. 2. Logan, M. E.; Goswami, R.; Tomczuk, B. R.; Venepalli, B. R. Ann. Rep. Med. Chem. 1991, 26, 43-51.
6. 3. Batt, A. R.; Kendrick, D. A.; Mathew, E.; Rooker, D. P.; Ryder, H., Sempte, G.; Szelke, M. Bioorg. Med. Chem. Lett. 1994, 4, 867-872.
7. 4. DiMaio, J.; Schiller, P. W.; Belleau, B. in Peptides: Structure and Biological Function, Proceedings of the 6th American Peptide Symposium, Pierce Chemical Company: 1979, 889.
8. 5. Lai, J. T. J. Org. Chem. 1980, 45, 754-755.
9. 6. (a) McCullough, K. J. Pyrazines and Related Ring Structures. In Rodd's Chemistry of Carbon Compounds; Elvesior Science: New York, 1989; pp. 294-296.
10. (b) Masuzawa, K.; Masaki, M.; Ohta, M. Bull Chem. Soc. Japan 1965, 38, 2078-2081.
11. (c) Masaki, V. M.; Ohta, M. Bull. Chem. Soc. Japan 1963, 36, 922-925.
12. (d) Martin, W. B.; Martell, A. E. J. Am. Chem. Soc. 1950, 72, 4301-4302.
13. 7. (a) Fobian, Y. M.; d'Avignon, A.; Moeller, K. D. Bioorg. Med. Chem. Letter 1996, 6, 315-318.
14. (b) Schanen, V.; Riche, C.; Chiaroni, A.; Quirion, J.-C.; Husson, H.-P. Tetrahedron Lett. 1994, 35, 2533-2536.
15. 8. (a) Suárez-Gea, M. L.; García-López, M. T.; González-Muñez, R.; Herrero, S.; Herranz, R. Tetrahedron Let. 1996, 37, 2083-2084.
16. (b) Jain, S.; Sujatha, K.; Rama Krishna, K. V.; Roy, R.; Singh, J.; Anand, N. Tetrahedron 1992, 48, 4985-4988.
17. (c) Bravo, A.; Gómez-Monterrey, I.; González-Muñiz, R.; García-López, M. T. J. Chem. Soc. Perkin Trans. I 1991, 3117-3120.
18. 9. (a) Lee, J.; Murray, W. V.; Rivero, R. A. J. Org. Chem. 1997, 62, 3874-3879.
19. (b) Goff, D. A.; Zuckermann, R. N. Tetrahedron. Lett. 1996, 37, 6247-6250.
20. 10. Fehrentz, J.-A.; Castro, B. Synthesis 1983, 676-678.
21. 11. For other examples of reactions of amines with serine derived β-lactones, see: (a) Cassidy, P. B.; Poulter, C. D. J. Am. Chem. Soc. 1996, 118, 8761-8762.
22. (b) Ratemi, E.; Vederas, J. C. Tetrahedron. Lett. 1994, 35, 7605-7608. S.
23. (c) Kucharczyk, N.; Badet, B.; Goffic, F. L. Synth. Comm. 1989, 19, 1603-1608.
24. (d) Arnold, L. D.; Kalantar, T. H., Vederas, J. C. J. Am. Chem. Soc. 1985, 107, 7105-7109.
25. 8: 766.4755, found: 766.4781.