Atom-economical synthesis of the N(10)-C(17) fragment of cyclotheonamides via a novel Passerini reaction-deprotection-acyl migration strategy1

Organic Letters

Volumn 3, Issue 21, 2001, Pages 3301-3304

  Owens, Timothy D ^a   Semple, J Edward ^a  

^a Dendreon   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTITHROMBIN; CYCLOPEPTIDE; CYCLOTHEONAMIDE A; CYCLOTHEONAMIDE C; CYCLOTHEONAMIDE D; CYCLOTHEONAMIDE E; CYCLOTHEONAMIDE E2; CYCLOTHEONAMIDE E3; PEPTIDE FRAGMENT; SERINE PROTEINASE INHIBITOR;

ACYLATION; ANIMAL; ARTICLE; CHEMISTRY; SPONGE (PORIFERA); SYNTHESIS;

ACYLATION; ANIMALS; ANTITHROMBINS; PEPTIDE FRAGMENTS; PEPTIDES, CYCLIC; PORIFERA; SERINE PROTEINASE INHIBITORS;

EID: 0035909598     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0165239     Document Type: Article

References (56)

1. Dedicated to Ruth F. Nutt, respected and admired mentor, on the occasion of her 60th birthday.
2. Semple, J. E. Abstracts of Papers, 219th National Meeting of the American Chemical Society, San Francisco, CA, March 26-30, 2000; American Chemical Society: Washington, DC, 2000; ORGN 667.
3. (a) α-Ketoamide serine protease inhibitors: Semple, J. E.; Levy, O. E.; Minami, N. K.; Owens, T. D.; Siev, D. V. Bioorg. Med. Chem. Lett. 2000, 10, 2305.
4. (b) Semple, J. E.; Rowley, D. C.; Brunck, T. K.; Ripka, W. C. Bioorg. Med. Chem. Lett. 1997, 7, 315.
5. (c) α-Ketoamide cysteine protease inhibitors: Nakamura, M.; Inoue, J.; Yamada, T. Bioorg. Med. Chem. Lett. 2000, 10, 2807.
6. (d) Otto, H. H.; Schirmeister, T. Chem. Rev., 1997, 97, 133.
7. NS3-4A Hepatitis C protease and inhibitors thereof: (a) Bennett, J. M. et al. Bioorg. Med. Chem. Lett. 2001, 11, 355.
8. (b) Hoofnagle, J. H.; Di Bisceglie, A. M. N. Engl. J. Med. 1997, 336, 347.
9. HIV protease inhibitors: Sheha, M. M.; Mahfouz, N. M.; Hassan, H. Y.; Youssef, A. F.; Mimoto, T.; Kiso, Y. Eur. J. Med. Chem. 2000, 35, 887.
10. Calpain inhibitors: (a) De Biasi, R. L.; Edelstein, C. L.; Sherry, B.; Tyler, K. L. J. Virol. 2001, 75, 351.
11. (b) Harbeson, S. L.; Abelleira, S. M.; Akiyama, A.; Barrett, R.; Carroll, R. M.; Straub, J. A.; Tkacz, J. N.; Wu, C.; Musso, G. J. Med. Chem. 1994, 37, 2918.
12. HCMV protease inhibitors: LaPlante, S. R.; Bonneau, P. R.; Aubry, N.; Cameron, D. R.; Deziel, R.; Grande-Maitre, C.; Plouffe, C.; Tong, L.; Kawai, S. H. J. Am. Chem. Soc. 1999, 121, 2974.
13. (a) CtA and CtB: Fusetani, N.; Matsunaga, S.; Matsumoto, H.; Takebayashi, Y. J. Am. Chem. Soc. 1990, 112, 7053.
14. (b) CtC, CtD, and CtE: Nakao, Y.; Matsunaga, S.; Fusetani, N. Bioorg. Med. Chem. 1995, 3, 1115.
15. (c) CtE2 and CtE3: Nakao, Y.; Oku, N.; Matsunaga, S.; Fusetani, N. J. Nat. Prod. 1998, 61, 667.
16. (a) Maryanoff, B. E.; Qui, X.; Padmanabhan, K. P.; Tulinsky, A.; Almond, H. R.; Andrade-Gordon, P.; Greco, M. N.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A.; Brungs, P. H.; Fusetani, N. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8048.
17. (b) Lewis, S. D.; Ng, A. S.; Baldwin, J. J.; Fusetani, N.; Naylor, A. M.; Shafer, J. A. Thrombosis Res. 1993, 70, 173.
18. Cyclotheonamides, total synthesis: (a) Bastiaans, H. M. M.; van der Baan, J. L.; Ottenheijm, H. C. J. J. Org. Chem. 1997, 62, 3880.
19. (b) Deng, J.; Hamada, Y.; Shioiri, T. Tetrahedron Lett. 1996, 37, 2261.
20. (c) Maryanoff, B. E.; Greco, M. N.; Zhang, H. C.; Andrade-Gordon, P.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A.; Brungs, P. H. J. Am. Chem. Soc. 1995, 117, 1225.
21. (d) Wipf, P.; Kim, H. J. Org. Chem. 1993, 58, 5592.
22. (e) Hagihara, M.; Schreiber, S. L. J. Am. Chem. Soc. 1992, 114, 6570.
23. Total synthesis of the PEP inhibitor Eurystatin A: Owens, T. D.; Araldi, G. L.; Nutt, R. F.; Semple, J. E. Tetrahedron Lett. 2001, 42, 6271.
24. Thrombin inhibitors: (a) Reiner, J. E.; Lim-Wilby, M. S.; Brunck, T. K.; Uong, T. H.; Goldman, E. A.; Abelman, M. A.; Nutt, R. F.; Semple, J. E.; Tamura S. Y. Bioorg. Med. Chem. Lett. 1999, 9, 895.
25. (b) Semple, J. E. Tetrahedron Lett. 1998, 39, 6645.
26. (c) Semple, J. E.; Rowley, D. C.; Brunck, T. K.; Uong, T. H.; Minami, N. K.; Owens, T. D.; Tamura, S. Y.; Goldman, E. A.; Siev, D. V.; Ardecky, R. J.; Carpenter, S. H.; Ge, Y.; Richard, B. M.; Hakanson, K.; Tulinsky, A.; Nutt, R. F.; Ripka, W. C. J. Med. Chem. 1996, 39, 4531.
27. FXa inhibitors: (a) Tamura, S. Y.; Levy, O. E.; Reiner, J. E.; Uong, T. H.; Goldman, E. A.; Brunck, T. K.; Semple, J. E. Bioorg. Med. Chem. Lett. 2000, 10, 745.
28. (b) Ho, J. Z.; Levy, O. E.; Gibson, T. S.; Nguyen, K.; Semple, J. E. Bioorg. Med. Chem. Lett. 1999, 9, 3459.
29. (c) Tamura, S. Y.; Goldman, E. A.; Bergum, P. W.; Semple, J. E. Bioorg. Med. Chem. Lett. 1999, 9, 2573.
30. uPA inhibitors: (a) Tamura, S. Y.; Weinhouse, M. I.; Roberts, C. A.; Goldman, E. A.; Masukawa, K.; Anderson, S. M.; Cohen, C. R.; Bradbury, A. E.; Bernadino, V. T.; Dixon, S. A.; Ma, M. G.; Nolan, T. G.; Brunck, T. K. Bioorg. Med. Chem. Lett. 2000, 10, 983.
31. Passerini reaction: (a) Passerini, M. Gazz. Chim. Ital. 1921, 51, 126.
32. (b) Passerini, M.; Ragni, G. Gazz. Chim. Ital. 1931, 61, 964.
33. (c) Authoritative review: Ugi, I. In Isonitrile Chemistry; Ugi, I., Ed.; Academic Press: New York, 1971; Chapter 7.
34. (d) TiCl4 activation: Carofiglio, T. et al. Organometallics 1993, 12, 2726.
35. (e) Seebach, D.; Adam, G.; Gees, T.; Schiess, M.; Weigand, W. Chem. Ber. 1988, 121, 507.
36. (f) Seebach, D.; Schiess, M. Helv. Chim. Acta 1983, 66, 1618.
37. Semple, J. E.; Levy, O. E. PCT Int. Appl. WO 0035868 A2, June, 2000.
38. Semple, J. E.; Owens, T. D.; Nguyen, K.; Levy, O. E. Org. Lett. 2000, 2, 2769.
39. Banfi, L.; Guanti, G.; Riva, R. Chem. Commun. 2000, 985.
40. All new compounds were characterized by full spectroscopic (NMR, low/high resolution MS) analysis. Yields refer to spectroscopically and chromatographically homogeneous (≥95% by HPLC, TLC) materials.
41. Tamura, S. Y.; Semple, J. E.; Ardecky, R. J.; Leon, P.; Carpenter, S. H.; Ge, Y.; Shamblin, B. M.; Weinhouse, M. I.; Ripka, W. C.; Nutt, R. F. Tetrahedron Lett. 1996, 37, 4109.
42. (a) Parikh, J. R.; Doering, W. V. E. J. Am. Chem. Soc. 1967, 89, 5505.
43. (b) Reviews: Tidwell, T. T. Synthesis 1990, 857.
44. (c) Tidwell, T. T. Org. React. 1990, 39, 297.
45. (d) Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
46. (a) Skorna, G.; Ugi, I. Angew. Chem., Int. Ed. Engl. 1977, 16, 259.
47. (b) Giesemann, G.; von Hinrichs, E.; Ugi, I. J. Chem Res. (S) 1982, 79.
48. (c) Periasamy, M. P.; Walborsky, H. M. Org. Prep. Proced. Int. 1979, 11, 293.
49. Dipeptide isonitriles prepared by this method retain their chiral integrity: Urban, R.; Marquarding, D.; Seidel, P.; Ugi, I. Chem. Ber. 1977, 110, 2012.
50. 1H), 2.70-2.89 (complex br m, 1H), 2.95 (m, 1H), 3.02-3.25 (complex m, 4H), 3.39-3.59 (m, 2H), 3.68 + 3.72 (major + minor s, 3H, ratio ∼1.4-1.6:1), 3.88 + 4.01 (2m, 1H), 4.40 (m, 1H), 4.50 (m, 2H), 4.57-4.76 (complex m, 2H), 5.03 + 5.11 (minor + major m, 1H α-CHO-acyl methine, ratio 1:2), 5.16-5.37 (m, 2H), 5.25 + 5.27 (2s, 2H), 5.85 + 5.97 (minor + major m, 1H), 6.95 (m, 2H), 7.03-7.14 (m, 4H), 7.16-7.29 (m, 3H), 7.35 (m, 1H), 7.44 (m, 2H).
51. 3OD): δ 1.30-1.45 (br m, 1H), 1.48-1.75 (br m, 3H), 1.94 (m, 2H), 2.07 (m, 1H), 2.32 (br m, 1H), 2.70-3.04 (complex m, 3H), 3.07-3.28 (complex m, 3H), 3.48-3.62 (m, 2H), 3.67 (m, 1H), 3.70 + 3.72 (2s, 3H), 4.05-4.13 (m, 1H), 4.37-4.57 (m, 2H), 4.60-4.78 (complex m, 3H), 5.18-5.40 (complex m, 2H), 5.23+ 5.25 (2s, 2H), 5.86 + 5.96 (minor + major m, 1H), 6.96 (m, 2H), 7.05-7.30 (m, 7H), 7.35 (m, 1H), 7.43 (m, 2H).
52. Elaboration of 14 to the corresponding protected vinylogous tyrosine (v-Tyr) intermediate could proceed via the following sequence of reactions: (a) TBDMSCl, imidazole, DMF, room temperature;
53. (b) LiBH4, THF, EtOH, 0°C to room temperature;
54. 3N, 5°C to room temperature;
55. 2, 0°C to room temperature. Alternatively, construction of the corresponding v-Tyr analogue of 12 followed by application of the Passerini reaction, deprotection, and O-to N-acyl migration sequence may also be a viable approach to this intermediate.
56. For application of MCR to synthesis of macrocyclic peptides and natural products, see: Doemling, A. Comb. Chem. High Throughput Screen. 1998, 1, 1 and references therein.