Total synthesis of the cyclic biphenyl ether peptides K-13 and OF494-III via S(N)Ar macrocyclizations of peptidyl ruthenium π-arene complexes

Journal of the American Chemical Society

Volumn 119, Issue 28, 1997, Pages 6488-6495

  Janetka, James W ^a,b   Rich, Daniel H ^a  

^a UNIVERSITY OF WISCONSIN MADISON   (United States)

^b NATIONAL INSTITUTE OF DIABETES AND DIGESTIVE AND KIDNEY DISEASES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DIPEPTIDYL CARBOXYPEPTIDASE INHIBITOR; K 13; MACROCYCLIC COMPOUND; OF 4949 I; OF 4949 II; OF 4949 III; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; COMPLEX FORMATION; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030861476     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja970614c     Document Type: Article

References (57)

1. (a) Kase, H.; Kaneko, M.; Yamada, K. J. Antibiot. 1987, 40, 450-454.
2. (b) Yasuzawa, T.; Shirahata, K.; Sano, H. J. Antibiot. 1987, 40, 455-458.
3. (a) Sano, S.; Ikai, K.; Kuroda, H.; Nakamura, T.; Obayashi, A.; Ezure, Y.; Enomoto, H. J. Antibiot. 1986, 39, 1674-1684.
4. (b) Sano, S.; Ikai, K.; Katayama, K.; Takesako, K.; Nakamura, T.; Obayashi, A.; Ezure, Y.; Enomoto, H. J. Antibiot. 1986, 39, 1685-1696.
5. (c) Sano, S.; Ueno, M.; Katayama, K.; Nakamura, T.; Obayashi, A. J. Antibiot. 1986, 39, 1697-1703.
6. (d) Sano, S.; Ikai, K.; Yoshikawa, Y.; Nakamura, T.; Obayashi, A. J. Antibiot. 1987, 40, 512-518.
7. (e) Sano, S.; Kuroda, H.; Ueno, M.; Yoshikawa, Y.; Nakamura; T.; Obayashi; A. J. Antibiot. 1987, 40, 519-525.
8. Frye, S. C. Methods Enzymol. 1984, 107, 388.
9. (a) Janetka, J. W.; Satyshur, K.; Rich, D. H. Acta Crystallogr., Sect. C 1996, 52, 3112-3114.
10. (b) Janetka, J. W.; Raman, P.; Satyshur, K.; Flentke, G. R.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 441-442.
11. Boger, D. L.; Yohannes, D. Biomed. Chem. Lett. 1993, 3, 245-250.
12. Rao, A. V. R.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev. 1995, 95, 2135-2167 and references within.
13. (a) Evans, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1989, 111, 1063-1072.
14. (b) Boger, D. L.; Yohannes, D. J. Org. Chem. 1989, 54, 2498-2502.
15. Intramolecular Ullmann condensation: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. Thalium trinitrate (TTN) mediated cyclization: (b) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (c) Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8621-8624.
16. Intramolecular Ullmann condensation: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. Thalium trinitrate (TTN) mediated cyclization: (b) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (c) Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8621-8624.
17. Intramolecular Ullmann condensation: (a) Boger, D. L.; Yohannes, D. J. Am. Chem. Soc. 1991, 113, 1427-1429. Thalium trinitrate (TTN) mediated cyclization: (b) Inoue, T.; Sasaki, T.; Takayanagi, H.; Harigaya, Y.; Hoshino, O.; Hara, H.; Inaba, T. J. Org. Chem. 1996, 61, 3936-3937. (c) Nakamura, K.; Nishiyama, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 8621-8624.
18. NAr Cyclization: Zhu, J. P. Synlett 1997, 133 and references within.
19. For other recent studies on novel approaches to biaryl ether formation, see: (a) Jung, M. E.; Jachiet, D.; Khan, S. I.; Kim, C. Tetrahedron Lett. 1995, 36, 361-364. (d) Jung, M. E.; Starkey, L. S. Tetrahedron Lett. 1995, 36, 7363-7366. (e) Feng, X.; Olsen, R. K. Tetrahedron Lett. 1991, 32, 5721-5724. (f) Feng, X.; Olsen, R. K. J. Org. Chem. 1992, 57, 5811-5812. (g) Moreau, P.; Guillaumet, G.; Coudert, G. Tetrahedron 1994, 50, 3407-3414. (h) Olsen, R. K.; Feng, X.; Campbell, M.; Shano, R.; Math, S. K. J. Org. Chem. 1995, 60, 6025-6031.
20. For other recent studies on novel approaches to biaryl ether formation, see: (a) Jung, M. E.; Jachiet, D.; Khan, S. I.; Kim, C. Tetrahedron Lett. 1995, 36, 361-364. (d) Jung, M. E.; Starkey, L. S. Tetrahedron Lett. 1995, 36, 7363-7366. (e) Feng, X.; Olsen, R. K. Tetrahedron Lett. 1991, 32, 5721-5724. (f) Feng, X.; Olsen, R. K. J. Org. Chem. 1992, 57, 5811-5812. (g) Moreau, P.; Guillaumet, G.; Coudert, G. Tetrahedron 1994, 50, 3407-3414. (h) Olsen, R. K.; Feng, X.; Campbell, M.; Shano, R.; Math, S. K. J. Org. Chem. 1995, 60, 6025-6031.
21. For other recent studies on novel approaches to biaryl ether formation, see: (a) Jung, M. E.; Jachiet, D.; Khan, S. I.; Kim, C. Tetrahedron Lett. 1995, 36, 361-364. (d) Jung, M. E.; Starkey, L. S. Tetrahedron Lett. 1995, 36, 7363-7366. (e) Feng, X.; Olsen, R. K. Tetrahedron Lett. 1991, 32, 5721-5724. (f) Feng, X.; Olsen, R. K. J. Org. Chem. 1992, 57, 5811-5812. (g) Moreau, P.; Guillaumet, G.; Coudert, G. Tetrahedron 1994, 50, 3407-3414. (h) Olsen, R. K.; Feng, X.; Campbell, M.; Shano, R.; Math, S. K. J. Org. Chem. 1995, 60, 6025-6031.
22. For other recent studies on novel approaches to biaryl ether formation, see: (a) Jung, M. E.; Jachiet, D.; Khan, S. I.; Kim, C. Tetrahedron Lett. 1995, 36, 361-364. (d) Jung, M. E.; Starkey, L. S. Tetrahedron Lett. 1995, 36, 7363-7366. (e) Feng, X.; Olsen, R. K. Tetrahedron Lett. 1991, 32, 5721-5724. (f) Feng, X.; Olsen, R. K. J. Org. Chem. 1992, 57, 5811-5812. (g) Moreau, P.; Guillaumet, G.; Coudert, G. Tetrahedron 1994, 50, 3407-3414. (h) Olsen, R. K.; Feng, X.; Campbell, M.; Shano, R.; Math, S. K. J. Org. Chem. 1995, 60, 6025-6031.
23. For other recent studies on novel approaches to biaryl ether formation, see: (a) Jung, M. E.; Jachiet, D.; Khan, S. I.; Kim, C. Tetrahedron Lett. 1995, 36, 361-364. (d) Jung, M. E.; Starkey, L. S. Tetrahedron Lett. 1995, 36, 7363-7366. (e) Feng, X.; Olsen, R. K. Tetrahedron Lett. 1991, 32, 5721-5724. (f) Feng, X.; Olsen, R. K. J. Org. Chem. 1992, 57, 5811-5812. (g) Moreau, P.; Guillaumet, G.; Coudert, G. Tetrahedron 1994, 50, 3407-3414. (h) Olsen, R. K.; Feng, X.; Campbell, M.; Shano, R.; Math, S. K. J. Org. Chem. 1995, 60, 6025-6031.
24. For other recent studies on novel approaches to biaryl ether formation, see: (a) Jung, M. E.; Jachiet, D.; Khan, S. I.; Kim, C. Tetrahedron Lett. 1995, 36, 361-364. (d) Jung, M. E.; Starkey, L. S. Tetrahedron Lett. 1995, 36, 7363-7366. (e) Feng, X.; Olsen, R. K. Tetrahedron Lett. 1991, 32, 5721-5724. (f) Feng, X.; Olsen, R. K. J. Org. Chem. 1992, 57, 5811-5812. (g) Moreau, P.; Guillaumet, G.; Coudert, G. Tetrahedron 1994, 50, 3407-3414. (h) Olsen, R. K.; Feng, X.; Campbell, M.; Shano, R.; Math, S. K. J. Org. Chem. 1995, 60, 6025-6031.
25. (a) Pearson, A. J.; Park, J. G.; Yang, S. H.; Chuang, Y.-H. J. Chem. Soc., Chem. Commun. 1989, 1363-1364.
26. (b) Pearson, A. J.; Park, J. G. J. Org. Chem. 1992, 57, 1744-1752.
27. (c) Pearson, A. J.; Lee, K. J. Org. Chem. 1994, 59, 2304-2313.
28. (d) Pearson, A. J.; Lee, K. J. Org. Chem. 1995, 60, 7153-7160.
29. (e) Pearson, A. J.; Bignan, G. Tetrahedron. Lett. 1996, 37, 735-738.
30. (f) Pearson, A. J.; Zhang, P.; Lee, K. J. Org. Chem. 1996, 61, 6581-6586.
31. (a) Pearson, A. J.; Lee, K. J. Org. Chem. 1994, 59, 2314-2323.
32. (b) Pearson, A. J.; Shin, H. Tetrahedron 1992, 48, 7527-7538.
33. (c) Pearson, A. J.; Bruhn, P. R. J. Org. Chem. 1991, 56, 7092-7097.
34. Pearson, A. J.; Park, J. G.; Zhu, P. Y. J. Org. Chem. 1992, 57, 3583-3589.
35. Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1995, 117, 10585-10586.
36. Pearson, A. J.; Bignan, G.; Zhang, P.; Chelliah, M. J. Org. Chem. 1996, 61, 3940-3941.
37. Synthesized according to Gill and Mann: Gill, T. P.; Mann, K. R. Organometallics 1982, 1, 485-488.
38. Synthesized independently by Amy Elder, University of Wisconsin-Madison, Department of Chemistry.
39. Details on the synthesis of dipeptide and amino acid starting materials are described in the Supplementary Information.
40. For recent reviews, see: (a) Semmelhack, M. F. Transition Metal Arene Complexes: Nucleophilic Addition. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergammon Press: New York, 1995, Vol. 12, Chapter 9.1, pp 979-1014. For recent studies, see: (b) Gill, U. S.; Moriarty, R. M.; Ku, Y. Y.; Butler, I. R. J. Organomet. Chem. 1991, 417, 313-325. (c) Lomenzo, S. A.; Nolan, S. P.; Trudell, M. L. Organometallics 1994, 13, 676-681.
41. For recent reviews, see: (a) Semmelhack, M. F. Transition Metal Arene Complexes: Nucleophilic Addition. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergammon Press: New York, 1995, Vol. 12, Chapter 9.1, pp 979-1014. For recent studies, see: (b) Gill, U. S.; Moriarty, R. M.; Ku, Y. Y.; Butler, I. R. J. Organomet. Chem. 1991, 417, 313-325. (c) Lomenzo, S. A.; Nolan, S. P.; Trudell, M. L. Organometallics 1994, 13, 676-681.
42. For recent reviews, see: (a) Semmelhack, M. F. Transition Metal Arene Complexes: Nucleophilic Addition. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergammon Press: New York, 1995, Vol. 12, Chapter 9.1, pp 979-1014. For recent studies, see: (b) Gill, U. S.; Moriarty, R. M.; Ku, Y. Y.; Butler, I. R. J. Organomet. Chem. 1991, 417, 313-325. (c) Lomenzo, S. A.; Nolan, S. P.; Trudell, M. L. Organometallics 1994, 13, 676-681.
43. (a) Moriarty, R. M.; Ku, Y.-Y.; Gill, U. S. J. Chem. Soc., Chem. Commun. 1987, 1837-1838.
44. (b) Sheldrick, W. S.; Gleichmann, A. J. Organomet. Chem. 1994, 470, 183-187.
45. (c) Gleichmann, A. J.; Wolff, J. M.; Sheldrick, W. S. J. Chem. Soc., Dalton Trans. 1995, 1549-1554.
46. An unsuccessful attempt at selectively complexing an arene in the presence of a free amine has been described: see ref 19c.
47. (a) Hunter, C. A.; Sanders, J. K. M J. Am. Chem. Soc. 1990, 112, 5525-5534.
48. (b) Burley, S. K.; Petsko, G. A. Science 1985, 229, 23-28.
49. (c) Morkuma, K. Acc. Chem. Res. 1977, 10, 294-300.
50. (d) Shetty, A. S.; Zhang, J.; Moore, J. S. J. Am. Chem. Soc. 1996, 118, 1019-1027.
51. Newcomb, L. F.; Haque, T. S.; Gellman, S. H. J. Am. Chem. Soc. 1995, 117, 6509-6519 and references within.
52. Abromovitch, R. A.; Shi, Q. Heterocycles 1994, 38, 2147-2151.
53. (a) Krämer, R. Angew. Chem., Intl. Ed. Engl. 1996, 35, 1197-1199.
54. (b) Jaouen, G.; Vessieres, A.; Butler, I. S. Acc. Chem. Res. 1993, 26, 361-369.
55. (c) Aronson, B.; Enmon, J. L.; Izenwasser, S.; Katz, J. L.; Kelkar, S. V.; Luo, L. B.; Nolan, S. P.; Trudell, M. L. J. Med. Chem. 1996, 39, 1560-1563.
56. (a) Gordon, E. M.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gallop, M. A. J. Med. Chem. 1994, 37, 1385-1401.
57. (b) Gallop, M. A.; Barret, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233-1251.