Synthesis of peptidomimetics containing a β-lactam moiety using peptidic diazoketones and imines in a staudinger reaction

Organic Letters

Volumn 1, Issue 6, 1999, Pages 869-871

  Linder, Michael R ^a   Podlech, Joachim ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000893663     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9908171     Document Type: Article

References (36)

1. (a) Podlech, J. Synlett 1996, 582.
2. (b) Podlech, J.; Under, M. R. J. Org. Chem. 1997, 62, 5873.
3. (c) Podlech, J.; Linder, M. R. In New Perspectives in Bioorganic Chemistry: Diederichsen, U., Lindhorst, T. K., Westermann, B., Wessjohann, L., Eds.; Wiley-VCH: Weinheim, 1999; in press.
4. (d) Podlech, J.; Steurer, S. Synthesis 1999, 650.
5. (a) Podlech, J.; Seebach, D. Angew. Chem. 1995, 107, 507; Angew. Chem., Int. Ed. Engl. 1995, 34, 471.
6. (a) Podlech, J.; Seebach, D. Angew. Chem. 1995, 107, 507; Angew. Chem., Int. Ed. Engl. 1995, 34, 471.
7. (b) Podlech, J.; Seebach, D. Liebigs Ann. 1995, 1217.
8. (c) Guibourdenche, C.; Podlech, J.; Seebach, D. Liebigs Ann. 1996, 1121.
9. (d) Matthews, J. L.; Braun, C.; Guibourdenche, C.; Overhand, M.; Seebach, D. In Enantioselective Synthesis of β-Amino Acids; Juaristi, E., Ed.; Wiley-VCH; New York, 1997; p 105.
10. Page, M. I. The Chemistry of β-Lactams; Blackie Academic & Professional: London, 1992.
11. (a) Di Modugno, E.; Erbetti, I.; Ferrari, L.; Galassi, G.; Hammond, S. M.; Xerri, L. Antimicrob. Agents Chemother. 1994, 38, 2362.
12. (b) Wise, R.; Andrews, J. M.; Brenwald, N. Antimicrob. Agents Chemother. 1996, 40, 1248.
13. (c) Singh, K. V.; Coque, T.; Murray, B. E. Antimicrob. Agents Chemother. 1996, 40, 2142.
14. (a) Nishimura, T.; Igarashi, J.-E.; Sasaki, A.; Sunagawa, M. Bioorg. Med. Chem. 1998, 6, 367.
15. (b) Shin, K. J.; Yoo, K. H.; Kim, D. J.; Park, S. W.; Ko, B. S.; Lee, S. J.; Huh, J. D.; Park, S. Y. Bioorg. Med. Chem. Lett. 1998, 8, 1607.
16. Georg, G. I.; Ravikumar, V. T. In The Organic Chemistry of β-Lactams; Georg, G. I., Ed.; VCH: New York, 1993; p 295.
17. (a) Srivastava, L. K.; Bajwa, S. B.; Johnson, R. L.; Mishra, R. K. J. Neurochem. 1988, 50, 960.
18. (b) Sreenivasan, U.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1993, 36, 256.
19. (c) Yu, K. L.; Rajakumar, G.; Srivastava, L. K.; Mishra, R. K.; Johnson, R. L. J. Med. Chem. 1988, 31, 1430.
20. Caution: The generation and handling of diazomethane requires special precaution: DeBoer, T. J.; Backer, H. J. Organic Syntheses; Wiley: New York, 1963; Collect. Vol. 4, p 250.
21. Common abbreviations for amino acids and protecting groups were used: Tle = tert-leucine. Eur. J. Biochem. 1984, 138, 9.
22. Juday, R.; Adkins, H. J. Am. Chem. Soc. 1955, 77, 4559.
23. D, and elemental analyses.
24. Texier-Boullet, F. Synthesis 1985, 679.
25. Krämer, B.; Franz, T.; Picasso, S.; Pruschek, P.; Jäger, V. Synlett 1997, 295.
26. (a) Drey, C. N. C.; Ridge, R. J.; Mtetwa, E. J. Chem. Soc., Perkin Trans. 1 1980, 378.
27. (b) Drey, C. N. C.; Ridge, R. J. J. Chem. Soc., Perkin Trans. 1 1981, 2468.
28. (c) Drey, C. N. C.; Mtetwa, E. J. Chem. Soc., Perkin Trans, 1 1982, 1587.
29. Allinger, N. L. J. Am. Chem. Soc. 1977, 99, 8127. The calculations have been performed with PCModel for Windows, version 6.00; Serena Software: Bloomington, IN, 1996.
30. (a) Richardson, J. S. In Advances in Protein Chemistry; Anfinsen, C. B., Edsall, J. T., Richards, F. M., Eds.; Academic Press: New York, 1981; Vol. 34, p 167.
31. (b) Ball, J. B.; Alewood, P. F. J. Mol. Recognit. 1990, 3, 55.
32. (c) Smith, J. A.; Pease, L. G. Crit. Rev. Biochem. 1980, 8, 315.
33. (a) Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bös, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039.
34. (b) Kessler, H. Angew. Chem. 1982, 94, 509; Angew. Chem., Int. Ed. Engl. 1982, 21, 512.
35. (b) Kessler, H. Angew. Chem. 1982, 94, 509; Angew. Chem., Int. Ed. Engl. 1982, 21, 512.
36. (c) Liskamp, R. M. J. Recl. Trav. Chim. Pays-Bas 1994, 113, 1.