Total synthesis of complestatin (chloropeptin II)

Angewandte Chemie - International Edition

Volumn 49, Issue 11, 2010, Pages 2018-2022

  Wang, Zhihui ^a   Bois Choussy, Michèle ^a   Jia, Yanxing ^a   Zhu, Jieping ^a  

^a CNRS   (France)

Author keywords

Chloropeptin I; Complestatin; Macrocycles; Peptides; Total synthesis

Indexed keywords

CHEMICAL EQUATIONS; CHLOROPEPTIN I; MACROCYCLES; SUZUKI-MIYAURA REACTION; TOTAL SYNTHESIS; TRIPEPTIDE;

PEPTIDES; SYNTHESIS (CHEMICAL);

CYCLIZATION;

ANTIINFECTIVE AGENT; CHLOROPHENOL; COMPLESTATIN; CYCLOPEPTIDE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; STREPTOMYCES; SYNTHESIS;

ANTI-BACTERIAL AGENTS; CHLOROPHENOLS; PEPTIDES, CYCLIC; STEREOISOMERISM; STREPTOMYCES;

EID: 77949385517     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.200906797     Document Type: Article

References (60)

1. I. Kaneko, D. T. Fearon, K. F. Austen, J. Immunol. 1980, 124, 1194-1198.
2. a) H. Seto, T. Fujioka, K. Furihata, I. Kaneko, S. Takahashi, Tetrahedron Lett. 1989, 30, 4987-4990;
3. b) I. Kaneko, K. Kamoshida, S. Takahashi, J. Antibiot. 1989, 42, 236-241.
4. a) K. Matsuzaki, H. Ikeda, T. Ogino, A. Matsumoto, H. B. Woodruff, H. Tanaka, S. Omura, J. Antibiot. 1994, 47, 1173-1174;
5. b) H. Tanaka, K. Matsuzaki, H. Nakashima, T. Ogino, A. Matsumoto, H. Ikeda, H. B. Woodruff, S. Omura, J. Antibiot. 1997, 58-65.
6. S. B. Singh, H. Jayasuriya, G. M. Salituro, D. L. Zink, A. Shafiee, B. Heimbuch, K. C. Silverman, R. B. Lingham, O. Genilloud, A. Teran, D. Vilella, P. Felock, D. Hazuda, J. Nat. Prod. 2001, 64, 874-882.
7. H. Gouda, K. Matsuzaki, H. Tanaka, S. Hirono, S. Omura, J. A. McCauley, P. A. Sprengeler, G. T. Furst, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 13087-13088.
8. a) V. R. Hegde, P. Dai, M. Patel, V. P. Gullo, Tetrahedron Lett. 1998, 39, 5683-5684;
9. b) H. Jayasuriya, G. M. Salituro, S. K. Smith, J. V. Heck, S. J. Gould, S. B. Singh, C. F. Homnick, M. K. Holloway, S. M. Pitzenberger, M. A. Patane, Tetrahedron Lett. 1998, 39, 2247-2248.
10. H.-T. Chiu, B. K. Hubbard, A. N. Shah, J. Eide, R. A. Fredenburg, C. T.Walsh, C. Khosla, Proc. Natl. Acad. Sci. USA 2001, 98, 8548-8553.
11. a) J. Zhu, Expert Opin. Ther. Pat. 1999, 9, 1005-1019;
12. b) K. C. Nicolaou, C. N. C. Boddy, S. Bräse, N.Winssinger, Angew. Chem. 1999, 111, 2230-2287;
13. Angew. Chem. Int. Ed. 1999, 38, 2096-2152;
14. c) D. H. Williams, B. Bardsley, Angew. Chem. 1999, 111, 1264-1286;
15. Angew. Chem. Int. Ed. 1999, 38, 1172-1193;
16. d) D. Bischoff, B. Bister, M. Bertazzo, V. Pfeifer, E. Stegmann, G. J. Nicholson, S. Keller, S. Pelzer, W. Wohlleben, R. D. Sussmüth, ChemBioChem 2005, 6, 267-272.
17. a) H. Tanaka, K. Matsuzaki, H. Nakashima, T. Ogino, A. Matsumoto, H. Ikeda, H. B. Woodruff, S. Omura, J. Antibiot. 1997, 50, 58-65;
18. b) K. Matsuzaki, T. Ogino, T. Sunazuka, H. Tanaka, S. Omura, J. Antibiot. 1997, 50, 66-69.
19. S. Y. Soo, B.-S. Yun, I.-J. Ryoo, J.-S. Choi, C.-K. Joo, S.-Y. Chang, J.-M. Chung, S. Oh, B. J. Gwag, I. D. Yoo, J. Pharmacol. Exp. Ther. 2001, 299, 377-384.
20. F. Dettner, A. Hänchen, D. Schols, L. Toti, A. Nuber, R. D. Süssmuth, Angew. Chem. 2009, 121, 1888-1893;
21. Angew. Chem. Int. Ed. 2009, 48, 1856-1861.
22. a) M. K. Gurjar, N. K. Tripathy, Tetrahedron Lett. 1997, 38, 2163-2166;
23. b) A.-C. Carbonnelle, E. G. Zamora, R. Beugelmans, G. Roussi, Tetrahedron Lett. 1998, 39, 4471-4472;
24. c) A. M. Elder, D. H. Rich, Org. Lett. 1999, 1, 1443-1446;
25. d) R. Beugelmans, G. Roussi, E. G. Zamora, A.-C. Carbonnelle, Tetrahedron 1999, 55, 5089-5112;
26. e) A. B. Smith III, J. J. Chruma, Q. Han, J. Barbosa, Bioorg. Med. Chem. Lett. 2004, 14, 1697-1702;
27. f) Y. Yamada, A. Akiba, S. Arima, C. Okada, K. Yoshida, F. Itou, T. Kai, T. Satou, K. Takeda, Y. Harigaya, Chem. Pharm. Bull. 2005, 53, 1277-1290;
28. g) Y. Yamada, S. Arima, C. Okada, A. Akiba, T. Kai, Y. Harigaya, Chem. Pharm. Bull. 2006, 54, 788-794.
29. H. Deng, J.-K. Jung, T. Liu, K.W. Kuntz, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2003, 125, 9032-9034.
30. T. Shinohara, H. Deng, M. L. Snapper, A. H. Hoveyda, J. Am. Chem. Soc. 2005, 127, 7334-7336.
31. J. Garfunkle, F. S. Kimball, J. D. Trzupek, S. Takizawa, H. Shimamura, M. Tomishima, D. L. Boger, J. Am. Chem. Soc. 2009, 131, 16036-16038.
32. N. Miyaura, A. Suzuki, Chem. Rev. 1995, 95, 2457-2483.
33. Y. Jia, M. Bois-Choussy, J. Zhu, Angew. Chem. 2008, 120, 4235-4240;
34. Angew. Chem. Int. Ed. 2008, 47, 4167-4172.
35. Y. Jia, M. Bois-Choussy, J. Zhu, Org. Lett. 2007, 9, 2401-2404.
36. a) J. Zhu, Synlett 1997, 133-134;
37. b) J. S. Sawyer, Tetrahedron 2000, 56, 5045-5065.
38. M. Bois-Choussy, unpublished results.
39. M. Bois-Choussy, R. Beugelmans, J. P. Bouillon, J. Zhu, Tetrahedron Lett. 1995, 36, 4781-4784.
40. a) M. Sakaitani, Y. Ohfune, J. Org. Chem. 1990, 55, 870-876;
41. b) A. J. Zhang, D. H. Russel, J. Zhu, K. Burgess, Tetrahedron Lett. 1998, 39, 7439-7442.
42. a) A.-C. Carbonnelle, J. Zhu, Org. Lett. 2000, 2, 3477-3480;
43. b) S. Boisnard, A.-C. Carbonnelle, J. Zhu, Org. Lett. 2001, 3, 2061-2064;
44. c) M. Bois-Choussy, P. Cristau, J. Zhu, Angew. Chem. 2003, 115, 4370-4373;
45. Angew. Chem. Int. Ed. 2003, 42, 4238-4241;
46. d) R. Lépine, J. Zhu, Org. Lett. 2005, 7, 2981-2984;
47. e) J. Dufour, L. Neuville, J. Zhu, Synlett 2008, 2355-2359.
48. M. H. Hansen, A. R. Harkness, D. S. Coffey, F. G. Bordwell, Y. Zhao, Tetrahedron Lett. 1995, 36, 8949-8952.
49. a) R. L. E. Furlan, E. G. Mata, O. A. Mascaretti, J. Chem. Soc. Perkin Trans. 1 1998, 355-358;
50. b) K. C. Nicolaou, A. A. Estrada, M. Zak, S. H. Lee, B. S. Safina, Angew. Chem. 2005, 117, 1402-1406;
51. Angew. Chem. Int. Ed. 2005, 44, 1378-1382.
52. a) R. Beugelmans, A. Bigot, J. Zhu, Tetrahedron Lett. 1994, 35, 7391-7394;
53. b) J. Zhu, R. Beugelmans, S. Bourdet, J. Chastanet, R. Georges, J. Org. Chem. 1995, 60, 6389-6396;
54. c) J. Zhu, T. Laïb, J. Chastanet, R. Beugelmans, Angew. Chem. 1996, 108, 2664-2666;
55. Angew. Chem. Int. Ed. Engl. 1996, 35, 2517-2519;
56. d) T. Temal-Laïb, J. Chastanet, J. Zhu, J. Am. Chem. Soc. 2002, 124, 583-590;
57. e) P. Cristau, J. P. Vors, J. Zhu, Tetrahedron Lett. 2003, 44, 5575-5578.
58. For size-selective cyclization reactions, see: a) A. Bigot, M. E. Tran Huu Dau, J. Zhu, J. Org. Chem. 1999, 64, 6283-6296;
59. For a review on conformation-directed macrocyclization reactions, see: b) J. Blankenstein, J. Zhu, Eur. J. Org. Chem. 2005, 1949-1964.
60. Hoffmann-La-Roche, Eur. Pat. Appl. 17.2070899, 2009.