Total synthesis of chloropeptin II (complestatin) and chloropeptin I

Journal of the American Chemical Society

Volumn 131, Issue 44, 2009, Pages 16036-16038

  Garfunkle, Joie ^a   Kimball, F Scott ^a   Trzupek, John D ^a   Takizawa, Shinobu ^a   Shimamura, Hiroyuki ^a   Tomishima, Masaki ^a   Boger, Dale L ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC NUCLEOPHILIC SUBSTITUTION REACTION; BICYCLIC STRUCTURE; CATALYZED CONVERSION; CHEMICAL EQUATIONS; ELECTROPHILIC REAGENTS; FUNCTIONALIZED; KEY ELEMENTS; KEY REACTIONS; MACRO-CYCLIZATION; PROTECTING GROUP; RING SYSTEMS; SINGLE-STEP; TERMINAL ALKYNE; TOTAL SYNTHESIS;

ACETYLENE; FLUORINE CONTAINING POLYMERS; SUBSTITUTION REACTIONS;

ETHERS;

CHLOROPEPTIN I; COMPLESTATIN;

ARTICLE; DRUG ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN IMMUNODEFICIENCY VIRUS INFECTION; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN BINDING; STREPTOMYCES; STRUCTURE ACTIVITY RELATION; TEMPERATURE MEASUREMENT;

CHLOROPHENOLS; CYCLIZATION; INDOLES; MACROCYCLIC COMPOUNDS; PEPTIDES, CYCLIC;

EID: 70450187429     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja907193b     Document Type: Article

References (48)

1. (a) Kaneko, I.; Fearon, D. T.; Austen, K. F. J. Immunol. 1980, 124, 1194-1198.
2. (b) Tachikawa, K.; Hasumi, K.; Endo, A. Thromb. Haemost. 1997, 77, 137-142.
3. (c) Tachikawa, K.; Hasumi, K.; Endo, A. Thrombosis Res. 1997, 87, 571-576.
4. Kaneko, I.; Kamoshida, K.; Takahashi, S. J. Antibiot. 1989, 42, 236-241.
5. Seto, H.; Fujioka, T.; Furihata, K.; Kaneko, I.; Takahashi, S. Tetrahedron Lett. 1989, 30, 4987-4990.
6. Momota, K.; Kaneko, I.; Kimura, S.; Mitamura, K.; Shimada, K. Biochem. Biophys. Res. Commun. 1991, 179, 243-250.
7. (a) Matsuzaki, K.; Ikeda, H.; Ogino, T.; Matsumoto, A.; Woodruff, H. B.; Tanaka, H.; Omura, S. J. Antibiot. 1994, 47, 1173-1174.
8. (b) Tanaka, H.; Matsuzaki, K.; Nakashima, H.; Ogino, T.; Matsumoto, A.; Ikeda, H.; Woodruff, H. B.; Omura, S. J. Antibiot. 1997, 50, 58-65.
9. (c) Matsuzaki, K.; Ogino, T.; Sunazuka, T.; Tanaka, H.; Omura, S. J. Antibiot. 1997, 50, 66-69.
10. Gouda, H.; Matsuzaki, K.; Tanaka, H.; Hirono, S.; Omura, S.; McCauley, J. A.; Sprengeler, P. A.; Furst, G. T.; Smith, A. B., III. J. Am. Chem. Soc. 1996, 118, 13087-13088.
11. (a) Jayasuriya, H.; Salituro, G. M.; Smith, S. K.; Heck, J. V.; Gould, S. J.; Singh, S. B.; Homnick, C. F.; Holloway, M. K.; Pitzenberger, S. M.; Patane, M. A. Tetrahedron Lett. 1998, 39, 2247-2248.
12. (b) Hegde, V. R.; Dai, P.; Patel, M.; Gullo, V. P. Tetrahedron Lett. 1998, 39, 5683-5684.
13. (a) Singh, S. B.; Jayasuriya, H.; Salituro, G. M.; Zink, D. L.; Shafiee, A.; Heimbuch, B.; Silverman, K. C.; Lingham, R. B.; Genilloud, O.; Teran, A.; Vilella, D.; Felock, P.; Hazuda, D. J. Nat. Prod. 2001, 64, 874-882.
14. (b) Singh, S. B.; Jayasuriya, H.; Hazuda, D. L.; Felock, P.; Homnick, C. F.; Sardana, M.; Patane, M. A. Tetrahedron Lett. 1998, 39, 8769-8770.
15. (a) Hegde, V. R.; Puar, M. S.; Dai, P. D.; Patel, M.; Gullo, V. P.; Chan, T.-M.; Silver, J.; Pramanik, B. N.; Jenh, C.-H. Bioorg. Med. Chem. Lett. 2003, 13, 573-575.
16. (b) Hegde, V. R.; Puar, M. S.; Dai, P.; Patel, M.; Gullo, V. P.; Pramanik, B. N.; Jenh, C.-H. Tetrahedron Lett. 2002, 43, 5339-5341.
17. Deng, H.; Jung, J.-K.; Liu, T.; Kuntz, K. W.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 9032-9034.
18. Shinohara, T.; Deng, H.; Snapper, M. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 7334-7336.
19. (a) Jia, Y.; Bois-Choussy, M.; Zhu, J. Angew. Chem., Int. Ed. 2008, 47, 4167-4172.
20. (b) Jia, Y.; Bois-Choussy, M.; Zhu, J. Org. Lett. 2007, 9, 2401-2404.
21. (c) Yamada, Y.; Akiba, A.; Arima, S.; Okada, C.; Yoshida, K.; Itou, F.; Kai, T.; Satou, T.; Takeda, K.; Harigaya, Y. Chem. Pharm. Bull. Jpn. 2005, 53, 1277-1290.
22. (d) Smith, A. B., III; Chruma, J. J.; Han, Q.; Barbosa, J. Bioorg. Med. Chem. Lett. 2004, 14, 1697-1702.
23. (e) Elder, A. M.; Rich, D. H. Org. Lett. 1999, 1, 1443-1446.
24. (f) Roussi, G.; Zamora, E. G.; Carbonnelle, A.-C.; Beugelmans, R. Heterocycles 1999, 51, 2041-2063.
25. (g) Kai, T.; Kajimoto, N.; Konda, Y.; Harigaya, Y.; Takayanagi, H. Tetrahedron Lett. 1999, 40, 6289-6292.
26. (h) Gurjar, M. K.; Tripathy, N. K. Tetrahedron Lett. 1997, 38, 2163-2166.
27. (a) Larock, R. C.; Yum, E. K. J. Am. Chem. Soc. 1991, 113, 6689-6690.
28. (b) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652-7662.
29. Shen, M.; Li, G.; Lu, B. Z.; Hossain, A.; Roschangar, F.; Farina, V.; Senanayaka, C. H. Org. Lett. 2004, 6, 4129-4132.
30. (a) Ma, C.; Liu, X.; Li, X.; Flippen-Anderson, J.; Yu, S.; Cook, J. M. J. Org. Chem. 2001, 66, 4525-4542.
31. See also: (b) Jeschke, T.; Wensbo, D.; Annby, U.; Gronowitz, S.; Cohen, L. A. Tetrahedron Lett. 1993, 34, 6471-6474.
32. Details are provided in Supporting Information.
33. (a) Boger, D. L.; Kim, S. H.; Mori, Y.; Weng, J.-H.; Rogel, O.; Castle, S. L.; McAtee, J. J. J. Am. Chem. Soc. 2001, 123, 1862-1871.
34. (b) Boger, D. L.; Kim, S. H.; Miyazaki, S.; Strittmatter, H.; Weng, J.-H.; Mori, Y.; Rogel, O.; Castle, S. L.; McAtee, J. J. J. Am. Chem. Soc. 2000, 122, 7416-7417.
35. Reddy, K. L.; Sharpless, K. B. J. Am. Chem. Soc. 1998, 120, 1207-1217.
36. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
37. Trzupek, J. D. Ph.D. Dissertation, 2006.
38. Jiang, W.; Wanner, J.; Lee, R. J.; Bounaud, P.-Y.; Boger, D. L. J. Am. Chem. Soc. 2002, 124, 5288-5290
39. and Jiang, W.; Wanner, J.; Lee, R. J.; Bounaud, P.-Y.; Boger, D. L. J. Am. Chem. Soc. 2003, 125, 1877-1887.
40. (a) Boger, D. L. Med. Res. Rev. 2001, 21, 356-381.
41. (b) Boger, D. L.; Miyazaki, S.; Kim, S. H.; Wu, J. H.; Loiseleur, O.; Castle, S. L. J. Am. Chem. Soc. 1999, 121, 3226-3227 and 10004-10011.
42. (c) Boger, D. L.; Castle, S. L.; Miyazaki, S.; Wu, J. H.; Beresis, R. T.; Loiseleur, O. J. Org. Chem. 1999, 64, 70-80.
43. (d) Boger, D. L.; Borzilleri, R. M.; Nukui, S.; Beresis, R. T. J. Org. Chem. 1997, 62, 4721-4736.
44. (e) Boger, D. L.; Borzilleri, R. M.; Nukui, S. Bioorg. Med. Chem. Lett. 1995, 5, 3091-3096.
45. (f) Boger, D. L.; Borzilleri, R. M. Bioorg. Med. Chem. Lett. 1995, 5, 1187-1190.
46. (g) Crowley, B. M.; Boger, D. L. J. Am. Chem. Soc. 2006, 128, 2885-2892.
47. Crowley, B. M.; Mori, Y.; McComas, C. C.; Tang, D.; Boger, D. L. J. Am. Chem. Soc. 2004, 126, 4310-4317.
48. Abbreviations: DEPBT, 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4-one; DtBPT, 1,1′-bis(di-tert-butylphosphino)ferrocene; EDCI, 1-[3-(dimethyl-amino)propyl]-3-ethylcarbodiimide hydrochloride; HOAt, 1-hydroxy- 7-azabenzotriazole; PyBOP, (benzotriazol-1-yl)tripyrrolidinophosphonium hexafluorophosphate.