Synthesis of cyclic peptides constrained with biarylamine linkers using Buchwald-Hartwig C-N coupling

Journal of Organic Chemistry

Volumn 71, Issue 23, 2006, Pages 8954-8956

  Balraju, V ^a,b   Iqbal, Javed ^a  

^a DR REDDY'S LABORATORIES LTD   (India)

^b UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CONFORMATIONS; NITROGEN COMPOUNDS; PALLADIUM; REACTION KINETICS; SYNTHESIS (CHEMICAL);

BIARYLAMINE LINKERS; BUCHWALD-HARTWIG C-N COUPLING; CYCLIC PEPTIDES; PEPTIDOMIMETICS;

AROMATIC COMPOUNDS;

AROMATIC AMINE; CARBON; CYCLOPEPTIDE; DIPEPTIDE; NITROGEN; PALLADIUM; TETRAPEPTIDE; TRIPEPTIDE;

ARTICLE; BUCHWALD HARTWIG COUPLING; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; MASS SPECTROMETRY; PEPTIDE SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

AMINES; MOLECULAR CONFORMATION; PEPTIDES, CYCLIC; STEREOISOMERISM;

EID: 33750884444     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061366i     Document Type: Article

References (43)

1. (a) Li, P.; Roller, P. P.; Xu, J. Curr. Org. Chem. 2002, 6, 411-440.
2. (b) Davies, J. S. J. Peptide Sci. 2003, 9, 471-501.
3. (c) Peng, L.; Roller, P. P. Curr. Top. Med. Chem. 2002, 2, 325-341.
4. (d) Wipf, P. Chem. Rev. 1995, 95, 2115.
5. (a) Alfonso, I. M.; Burguete, I.; Luis, S. V. J. Org. Chem. 2006, 71, 2242-2250.
6. (b) Billing, J. F.; Nilsson, U. J. J. Org. Chem. 2005, 70, 4847-4850.
7. (c) Punna, S.; Kuzelka, J.; Wang, Q.; Finn, M. G. Angew. Chem., Int. Ed. 2005, 44, 2215-2220.
8. (d) Fernández-López, S.; Kim, H.-S.; Choi, E. C.; Delgado, M.; Granja, J. R.; Khasanov, A.; Kraehenbuehl, K.; Long, G.; Weinberger, D. A.; Wilcoxen, K. M.; Ghadiri, M. R. Nature 2001, 412, 452-455.
9. (e) Loughlin, W. A.; Tyndall, J. D. A.; Glenn, M. P.; Fairlie, D. P. Chem. Rev. 2004, 104, 6085-6117.
10. (f) Reid, R. C.; Abbenante, G.; Taylor, S. M.; Fairlie, D. P. J. Org. Chem. 2003, 68, 4464-4471.
11. (g) Reyes, S. J.; Burgess, K. Tetrahedron: Asymmetry 2005, 16, 1061-1069.
12. (h) Singh, Y.; Stoermer, M. J.; Lucke, A. J.; Guthrie, T.; Fairlie, D. P. J. Am. Chem. Soc. 2005, 127, 6563-6572.
13. (i) Velasco-Torrijos, T.; Murphy, P. V. Org. Lett. 2004, 6, 3961-3964.
14. (j) Heinrichs, G.; Kubic, S.; Lacour, J.; Vial, L. J. Org. Chem. 2005, 70, 4498-4501
15. (k) Otto, S.; Kubik, S. J. Am. Chem. Soc. 2003, 125, 7804-7805.
16. (a) Reddy, P. R.; Balraju, V.; Madhavan, G. R.; Banerji, B.; Iqbal, J. Tetrahedron Lett. 2003, 44, 353-356.
17. (b) Balraju, V.; Reddy, D. S.; Periasamy, M.; Iqbal, J. J. Org. Chem. 2005, 70, 9626-9628.
18. (c) Balraju, V.; Reddy, D. S.; Periasamy, M.; Iqbal, J. Tetrahedron Lett. 2006, 47, 3569-3571.
19. (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131-209.
20. (b) Prim, D.; Campagne, J.-M.; Joseph, D.; Andrioletti, B. Tetrahedron 2002, 55, 2041-2075.
21. (c) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 2000, 65, 1144-1157.
22. (d) Yin, J.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 6043-6048.
23. (e) Hartwig, J. F.; Kawatsura, M.; Hauck, S. I.; Shaughnessy, K. H.; Alcazar-Roman, L. M. J. Org. Chem. 1999, 64, 5575-5580.
24. For examples of optimizations of palladium-catalyzed animations and amidations, see: (f) Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101-1104.
25. (g) Guari, Y.; van Es, D. S.; Reek, J. N. H.; Kamer, P. C. J.; van Leeuwen, P. W. N. M. Tetrahedron Lett. 1999, 40, 3789-3790.
26. (h) Yang, B. H.; Buchwald, S. L. Org. Lett. 1999, 1, 35-38.
27. (i) Browning, R. G.; Badarinarayana, V.; Mahmud, H.; Lovely, C. J. Tetrahedron 2004, 60, 359-365.
28. (j) Ferriera, I. C. F. R.; Queiroz, M. J. R. P.; Kirsch, G. Tetrahedron 2003, 59, 3737-3743.
29. (k) Prashad, M.; Mak, X. Y.; Liu, Y.; Repic, O. J. Org. Chem. 2003, 68, 1163-1164.
30. (l) Harris, M. C.; Huang, X. H.; Buchwald, S. L. Org. Lett. 2002, 4, 2885-2888.
31. (m) Klapars, A.; Antilla, J. C.; Huang, X.; Buchwald, S. L. J. Am. Chem. Soc. 2001, 123, 7727-7729.
32. (n) Shakespeare, W. C. Tetrahedron Lett. 1999, 40, 2035-2038.
33. (o) Wang, Z.; Skerlj, R. T.; Bridger, G. J. Tetrahedron Lett. 1999, 40, 3543-3546.
34. (p) Arterburn, J. B.; Rao, K. V.; Ramdas, R.; Dible, B. R. Org. Lett. 2001, 3, 1351-1354.
35. Pattarawarappan, M.; Zaccaro, M. C.; Saragovi, U. H.; Burgess, K. J. Med. Chem. 2002, 45, 4387-4390.
36. (a) Blankenstein, J.; Zhu, J. Eur. J. Org. Chem. 2005, 1949-1964.
37. (b) Nicolaou, K. C.; Mitchell, H. J.; Jain, N. F.; Winssinger, N.; Hughes, R.; Bando, T. Angew. Chem., Int. Ed. 1999, 38, 240-244.
38. (c) Williams, D. H.; Bardsley, B. Angew. Chem., Int. Ed. 1999, 38, 1172-1193.
39. (d) Pearson, A. J.; Bignan, G.; Zhang, P.; Chelliah, M. J. Org. Chem. 1996, 61, 3940-3941.
40. (e) Rao, A. V. R.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev. 1995, 95, 2135-2167.
41. Seebach, D.; Overhand, M.; Kuhnle, F. N. M.; Martinoni, B. Helv. Chim. Acta 1996, 79, 913-941.
42. (a) Shi, L.; Wang, M.; Fan, C.-A.; Zhang, F.-M.; Tu, Y.-Q. Org. Lett. 2003, 5, 3515-3517.
43. (b) March, J. Advanced Organic Chemistry, Reactions, Mechanisms and Structure, 4th ed.; John Wiley & Sons: New York, 1992; p 641.