Systematic study of the synthesis of macrocyclic dipeptide β-turn mimics possessing 8-, 9-, and 10- membered rings by ring-closing metathesis

Journal of Organic Chemistry

Volumn 70, Issue 10, 2005, Pages 3838-3844

  Kaul, Ramesh ^a   Surprenant, Simon ^a   Lubell, William D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC HYDROCARBONS; CATALYSTS; CHEMICAL BONDS; DERIVATIVES; NITROGEN COMPOUNDS; STRUCTURE (COMPOSITION); SYNTHESIS (CHEMICAL);

AMIDES; ENANTIOMERICAL FORMING; GRUBB'S CATALYSTS; MACROCYCLIC DIPEPTIDES;

POLYPEPTIDES;

ALKENE; ALLYLGLYCINE; AMIDE; BENZYL DERIVATIVE; DIPEPTIDE; LACTAM; MACROCYCLIC COMPOUND;

ARTICLE; BETA TURN; CATALYST; CIS TRANS ISOMERISM; ENANTIOMER; GEOMETRY; MOLECULAR MIMICRY; PEPTIDE SYNTHESIS; PROTEIN STRUCTURE; RING CLOSING METATHESIS;

BIOMIMETICS; CYCLIZATION; DIPEPTIDES; LACTAMS, MACROCYCLIC; PEPTIDES, CYCLIC; PROTEIN STRUCTURE, SECONDARY; STEREOISOMERISM;

EID: 18744403986     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0477648     Document Type: Article

References (65)

1. (a) Venkatachalam, C. M. Biopolymers 1968, 6, 1425.
2. (b) Suat, K. K.; Seetharama, D. S. J. Curr. Pharm. Des. 2003, 9, 1209.
3. (a) Wilmot, C. M.; Thornton, J. M. J. Mol. Biol. 1988, 203, 221.
4. (b) Lewis, P. N.; Momany, F. A.; Scheraga, H. A. Proc. Natl. Acad. Sci. U.S.A. 1971, 68, 2293.
5. (a) Hirschmann, R.; Nicolaou, K. C.; Pietranico, S.; Salvino, J.; Leahy, E. M.; Sprengler, P. A.; Furst, G.; Smith, A. B.; Strader, C. D.; Casieri, M. A.; Candelore, M. R.; Donaldson, G.; Maechler, L. J. Am. Chem. Soc. 1992, 114, 9217.
6. (b) Veber, D. F.; Freidinger, R. M.; Perlow, D. S.; Palevida, W. J., Jr.; Holly, F. W.; Strachan, R. G.; Nutt, R. F.; Arison, B. H.; Homnick, C.; Randall, W. C.; Glitzer, M. S.; Saperstein, R.; Hirschmann, R. Nature 1981, 292, 55.
7. (a) Lee, J. H.; Lim, S. K.; Huh, S. H.; Lee, D.; Lee, W. Eur J. Biochem. 1998, 51, 251.
8. (b) Zhang, J.; Xiong, C.; Ying, J.; Wang, W.; Hruby, V. J. Org. Lett. 2003, 5, 3115.
9. (a) Miskolzie, M.; Yamamoto, H.; York, E. J.; Stewart, J. M.; Kotovych, G. J. Biomol. Struct. Dyn. 2000, 17, 947.
10. (b) Sejbal, J.; Cann, J. R.; Stewart, J. M.; Gera, L.; Kotovych, G. J. Med. Chem. 1996, 39, 1281.
11. Freidinger, R. M.; Veber, D. F.; Perlow, D. S.; Brooks, J. R.; Saperstein, R. Science 1980, 210, 656.
12. (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H. G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
13. (b) Cluzeau, J.; Lubell, W. D. Biopolymers (Peptide Sci.) 2005, in press.
14. Halab, L.; Gosselin, F.; Lubell, W. D. Biopolymers (Peptide Sci.) 2000, 55, 101.
15. Gillespie, P.; Cicariello, J.; Olson, G. L. Biopolymers (Peptide Sci.) 1997, 43, 191.
16. (a) Belvisi, L.; Gennari, C.; Mielgo, A.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 1999, 389.
17. (b) Belvisi, L.; Gennari, C.; Madder, A.; Mielgo, A.; Potenza, D.; Scolastico, C. Eur. J. Org. Chem. 2000, 695.
18. (c) Belvisi, L.; Bernardi, A.; Manzoni, L.; Potenza, D.; Scolastico, C. J. Org. Chem. 2000, 65, 2563.
19. Halab, L.; Becker, J. A. J.; Darula, Z.; Tourwe, D.; Kieffer, B. L.; Simonin, F.; Lubell, W. D. J. Med. Chem. 2002, 45, 5353.
20. Belvisi, L.; Bernardi, A.; Checchia, A.; Manzoni, L.; Potenza, D.; Scolastico, C.; Castorina, M.; Cupelli, A.; Giannini, G.; Carminati, P.; Pisano, C. Org. Lett. 2001, 3, 1001.
21. (a) Illuminati, G.; Mandolini, L. Acc. Chem. Res. 1981, 14, 95.
22. (b) Evans, P. A.; Holmes, A. B. Tetrahedron 1991, 47, 9131.
23. Creighton, C. J.; Leo, G. C.; Du, Y.; Reitz, A. B. Bioorg. Med. Chem. 2004, 12, 4375.
24. (a) Derrer, S.; Davies, J. E.; Holmes, A. D. J. Chem. Soc., Perkin Trans 1 2000, 2943.
25. (b) Creighton, C. J.; Reitz, A. B. Org. Lett. 2001, 3, 893.
26. Derrer, S.; Davies, J. E.; Holmes, A. D. J. Chem. Soc., Perkin Trans 1 2000, 2957.
27. (a) Halab, L.; Lubell, W. D. J. Am. Chem. Soc. 2002, 124, 2474.
28. (b) Halab, L.; Lubell, W. D. J. Org. Chem. 1999, 64, 3312.
29. Banfi, L.; Basso, A.; Guanti, G.; Riva, R. Tetrahedron Lett. 2003, 44, 7655.
30. Fink, B. E.; Kym, P. R.; Katzenellenbogen, J. A. J. Am. Chem. Soc. 1998, 120, 4334.
31. Hofmann, T.; Waibel, R.; Gmeiner, P. J. Org. Chem. 2003, 68, 62.
32. (a) Trinka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
33. (b) Grubbs, R. H.; Blackwell, H. E. Angew. Chem., Int. Ed. 1898, 37, 3281.
34. (c) Ripka, A. S.; Bohacek, R. S.; Rich, D. H. Bioorg. Med. Chem. Lett. 1998, 8, 357.
35. (d) Stymiest, J. L.; Mitchell, B. F.; Wong, S.; Vederas, J. C. Org. Lett. 2003, 5, 47.
36. (e) Reichwein, J. F.; Versluis, C.; Liskamp, R. M. J. J. Org. Chem. 2000, 65, 6187.
37. (f) Schafmeister, C. E.; Po, J.; Verdine, G. L. J. Am. Chem. Soc. 2000, 122, 5891.
38. (a) Xu, P.-F.; Lu, T.-J. J. Org. Chem. 2003, 68, 658.
39. (b) Nájera, G. G. A. C. J. Org. Chem. 2000, 65, 7310.
40. (c) Myers, A. G.; Gleason, J. L. Org. Synth. 1999, 76, 57.
41. (d) Yeh, T.-L.; Liao, C.-C.; Uang, B.-J. Tetrahedron 1997, 53, 11141.
42. (e) Katagiri, N.; Okada, M.; Morishita, Y.; Kaneko, C. Tetrahedron 1997, 53, 5725.
43. (f) Hanessian, S.; Yang, R.-Y. Tetrahedron Lett. 1996, 37, 8997.
44. (g) Workman, J. A.; Garrido, N. P.; Sancon, J.; Roberts, E.; Wessel, H. P.; Sweeney, J. B. J. Am. Chem. Soc. 2005, 127, 1066.
45. (a) Gosselin, F.; Lubell, W. D. J. Org. Chem. 1998, 63, 7463.
46. (b) Swarbrick, M. E.; Gosselin, F.; Lubell, W. D. J. Org. Chem. 1999, 64, 1993.
47. Gmeiner, P.; Feldman, P. L.; Chu-Moyer, M. Y.; Rapoport, H. J. Org. Chem. 1990, 55, 3068.
48. Douat, C.; Heitz, A.; Martinez, J.; Fehrentz, J. A. Tetrahedron Lett. 2001, 42, 3319.
49. (a) Tarbell, D. S.; Yamamoto, Y.; Pope, B. M. Proc. Natl. Acad. Sci., U.S.A. 1972, 69, 730.
50. (b) Paquet, A. Can. J. Chem. 1982, 60, 976.
51. Rodríguez, A.; Miller, D. D.; Jackson, R. F. W. Org. Biomol. Chem. 2003, 1, 973.
52. Trost, B. M.; Rudd, M. T. Org. Lett. 2003, 5, 4599.
53. Pascal, R.; Sola, R. Tetrahedron Lett. 1998, 39, 5031.
54. Johnson, T.; Quibell, M.; Sheppard, R. C. J. Pept. Sci. 1995, 1, 11.
55. Miranda, L. P.; Meutermans, W. D. F.; Smythe, M. L.; Alewood, P. F. J. Org. Chem. 2000, 65, 5460.
56. Couplings were unsuccessful using (a) TBTU/DIEA/DCM, Knorr, R.; Trzeciak, A.; Bannwarth, W.; Gillessen, D. Tetrahedron Lett. 1989, 30, 1927.
57. 2, Castro, B.; Dormoy, J.-R.; Evin, G.; Selve, C. Tetrahedron Lett. 1975, 1219.
58. 2, Dourtoglou, C.; Ziegler, J. C.; Gross, B. Tetrahedron Lett. 1978, 1269.
59. 2, Sheehan, J. C.; Hess, G. P. J. Am. Chem. Soc. 1955, 77, 1067;
60. Konig, W.; Geiger, R. Chem. Ber. 1970, 103, 788.
61. Harayama, T.; Nakatsuka, K.; Nishioka, H.; Murakami, K.; Ohmori, Y.; Takeuchi, Y.; Ishii, H.; Kenmotsu, K. Heterocycles 1994, 38, 2729.
62. Fürstner, A.; Langemann, K. J. Am. Chem. Soc. 1997, 119, 9130.
63. Schlessinger, R. H.; Bebernitz, G. R.; Lin, P.; Poss, A. J. J. Am. Chem. Soc. 1985, 107, 1777.
64. Dinsmore, C. J.; Bergman, J. M.; Bogusky, M. J.; Culberson, J. C.; Hamilton, K. A.; Graham, S. L. Org. Lett. 2001, 3, 865.
65. Kaul, R.; Broullette, Y.; Sajjadi, Z.; Hansford, K. A.; Lubell, W. D. J. Org. Chem. 2004, 69, 6131.