Application of ring-closing metathesis to the synthesis of rigidified amino acids and peptides

Journal of the American Chemical Society

Volumn 118, Issue 40, 1996, Pages 9606-9614

  Miller, Scott J ^a   Blackwell, Helen E ^a   Grubbs, Robert H ^a  

^a California Institute of Technology ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PEPTIDE SYNTHESIS;

EID: 0029860486     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja961626l     Document Type: Article

References (73)

1. For a recent reviews on applications of olefin metathesis and related processes in organic synthesis, see: (a) Grubbs, R. H.; Pine, S. H. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 5, Chapter 9.3.
2. (b) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-552.
3. (c) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836.
4. For previous reports on RCM from this laboratory, see: (a) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 5426-5427.
5. (b) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Sac. 1992, 114, 7324-7325.
6. (c) Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 3800-3801.
7. (d) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857.
8. (e) Fujimura, O.; Fu, G. C.; Grubbs, R. H. J. Org. Chem. 1994, 59, 4029-4031.
9. (f) Kim, S. H.; Bowden, N.; Grubbs, R. H. J. Am. Chem. Soc. 1994, 115, 10680-10681.
10. (g) Miller, S. J.; Kim, S. H.; Chen, Z.-R.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 2108-2109.
11. (h) Coates, G. W.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 229-230.
12. (i) Fujimura, O.; Grubbs, R. G. J. Am. Chem. Soc. 1996, 118, 2499-2500.
13. (j) Kim, S. H.; Zuercher, W. J.; Bowden, N. B.; Grubbs, R. H. J. Org. Chem. 1996, 61, 1073-1081.
14. For the preparation and characterization of catalyst la, see: (a) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974-3975.
15. (b) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858-9859.
16. For the preparation and characterization of catalyst 1b, see: (c) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
17. (d) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
18. For recent applications of metathesis-based methods to natural product synthesis, see: (a) Martin, S. F.; Liao, Y.; Rein, T. Tetrahedron Lett. 199-4, 35, 691-694.
19. (b) Borer, B. C.; Deerenberg, S.; Bieraugel, H.; Pandit, U. K. Tetrahedron Lett. 1994, 35, 3191-3194.
20. (c) Morken, J. P.; Didiuk, M. T.; Visser, M. S.; Hoveyda, A. H. J. Am. Chem. Soc. 1994, 116, 3123-3124.
21. (d) Martin, S. F.; Wagman, A. S. Tetrahedron Lett. 1995, 36, 1169-1170.
22. (e) Houri, A. F.; Xu, Z.; Cogan, D.; Hoveyda, A. H. J. Am. Chem. Soc. 1995, 117, 2943-2944.
23. (f) Huwe, C. M.; Blechert, S. Tetrahedron Lett. 1995, 36, 1621-1624.
24. (g) Overkleeft, H. S.; Pandit, U. K. Tetrahedron Lett. 1996, 37, 547-550.
25. (h) Randall, M. L.; Tallarico, J. A.; Snapper, M. L. J. Am. Chem. Soc. 1995, 117, 9610-9611.
26. (i) Huwe, C. M.; Kiehl, O. C.; Blechert, S. Synlett 1996, 65-66.
27. (j) Fürstner, A.; Langemann, K. J. Org. Chem. 1996, 61, 3942-3943.
28. (a) Miller, S. J.; Grubbs, R. H. J. Am. Chem. Soc. 1995, 117, 5855-5856.
29. (b) Garro-Héllion, F.; Guibé, F. J. Chem. Soc., Chem. Commun. 1996. 641-642.
30. Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365.
31. For an overview of the field, see: (a) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699-1720.
32. (b) Tetrahedron Symposia-in-Print Number 50, M. Kahn, Ed.; 1993; Vol. 49, number 17.
33. (c) Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244-1267.
34. (d) Hruby, V. J.; AlObeidi, F.; Kazmierski, W. Biochem. J. 1990, 268, 249-262.
35. (e) Toniolo, C. Int. J. Pept. Protein Res. 1990, 35, 287-300.
36. Myers, A. G.; Gleason, J. L.; Yoon, T. Y. J. Am. Chem. Soc. 1995, 117, 8488-8489 and references therein.
37. Pietzonka, T.; Seebach, D. Angew. Chem. Int. Ed. Engl. 1992, 31, 1481-1482.
38. 13C NMR, IR, and mass spectral characteristics (see Experimetal Section). The cases involving C-allylglycine in Scheme 1 were performed on the racemic mixtures.
39. We have discussed this issue in more detail in ref 2g.
40. Vinyl glycine derivative 8 was prepared by derivatization of N-allylN-BOC-methionine methyl ester in analogy to the procedure of Rapoport, see: (a) Afzali-Ardakani, A.; Rapoport, H. J. Org. Chem. 1980, 45, 4817-4820.
41. (b) Meffre, P.; Voquang, L.; Voquang, Y.; Le Goffic, F. Synth. Commun. 1989, 19, 3457-3468.
42. A monocyclized product was identified by FABMS. No ions corresponding to the bicyclization product could be detected. The monocyclized product was formed at approximately the same rate as the six-membered cyclic product 5, and no other product was formed after elongated reaction time. The formation of cyclic product 5 was previously found to be fast and effectively irreversible. Thus, we believe that treatment of substrate 10 under the analogous reaction conditions leads to the sixmembered monocyclization product as opposed to the 11-membered monocyclization product.
43. (a) Musiol, H.-J.; Siedler, F.; Quarzago, D.; Moroder, L. Biopolymers 1994, 34, 1553-1562.
44. (b) Siedler, F.; Quarzago, D.; Rudolph-Bohner, S.; Moroder, L. Biopolymers 1994, 34, 1563-1572.
45. For discussions of β-turns in proteins, see: (a) Rizo, J.; Gierasch, L. M. Ann. Rev. Biochem. 1992, 61, 387-418.
46. (b) Rose, G. D.; Gierasch, L. M.; Smith, J. A. Adv. Protein Chem. 1985, 37, 1-109. For a review of β-turn mimetics, see: ref 7b.
47. Nutt, R. F.; Strachan, R. G.; Veber, D. F.; Holly, F. W. J. Org. Chem. Am. Chem. Soc. 1980, 45, 3078-3080.
48. Nutt, R. F.; Veber, D. F.; Saperstein, R. J. Am. Chem. Soc. 1980, 102, 6539-6545.
49. Ravi, A.; Balaram, P. Tetrahedron 1984, 40, 2577-2583.
50. The disulfide dihedral angle in 10 has been shown to be 82° with right-handed chirality in the solid state. Ravi. A.; Prasad, B. V.; Balaram, P. J. Am. Chem. Soc. 1983, 105, 105-109.
51. (a) Venkatachalapathi, Y. V.; Balaram, P. Biopolymers 1981, 20, 1137-1145.
52. (b) Prasad, B. V. V.; Balaram, H.; Balaram, P. Biopolymers 1982, 21, 1261-1273.
53. A related cyclization was performed with unprotected tyrosine which afforded the analogous macrocycle in 70% yield. The free phenol therefore does not interfere with catalyst activity.
54. 2, see: (a) Gellman, S. H.; Dado, G. P.; Liang, G.-B.; Adams, B. R. J. Am. Chem. Soc. 1991, 113, 1164-1173.
55. (b) Liang, G.-B.; Desper, J. M.; Gellman, S. H. J. Am. Chem. Soc. 1993, 115, 925-938.
56. (c) Gardner, R. R.; Liang, G.-B.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 3280-3281.
57. (d) Rao, C. P.; Nagaraj, R.; Rao, C. N. R.; Balaram, P. Biochemistry 1980, 19, 425-431.
58. See ref 19.
59. See ref 18.
60. The olefin geometry of 22 was not assigned.
61. For literature on cyclization reactions performed on solid-supportbound substrates, see: (a) Hiroshige, M.; Hauske, J. R.; Zhou, P. J. Am. Chem. Soc. 1995, 117, 11590-11591.
62. (b) Andreu, D.; Albericio, F.; Sole, N. A.; Munson, M. C.; Ferrer, M.; Barany, G. Methods Mol. Biol. (Totowa, NJ) 1994, 35 (Peptide Synthesis Protocols), 91.
63. (c) Bunin, B. A.; Plunkett, M. J.; Ellman, J. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4708-4712.
64. (d) Virgilio, A. A.; Ellman, J. A. J. Am. Chem. Soc. 1994, 116, 11580-11581.
65. (e) Zhao, Z.; Felix, A. M. Pept. Res. 1994, 7, 218-223.
66. (f) Albericia, F.; Hammer R. P.; Garciaechevaerria, C.; Mollins, M. A.; Chang, J. L.; Munson, M. C.; Pons, M.; Giralt, E.; Barany, G. Int. J. Pept. Protein Res. 1991, 37, 402-413.
67. (g) Apsimon, J. W.; Dixit, D. M. Can. J. Chem. 1982, 60, 368-370.
68. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923-2925.
69. See ref 3.
70. Bodansky, M. Peptide Chemistry; Springer-Verlag: New York, 1988, pp 55-146 and references therein.
71. 1H NMR. This impurity is not present in the cyclized product 16.
72. Merrified, R. B. J. Am. Chem. Soc. 1963, 85, 1476-1482.
73. Sarin, V. K.; Kent, S. B. H.; Tam, J. P.; Merrifield, R. B. Anal. Biochem. 1981, 117, 147-157.