Total synthesis of TMC-95A and -B via a new reaction leading to Z-enamides. Some preliminary findings as to SAR

Journal of the American Chemical Society

Volumn 126, Issue 20, 2004, Pages 6347-6355

  Lin, Songnian ^a   Yang, Zhi Qiang ^a   Kwok, Benjamin H B ^c   Koldobskiy, Michael ^c   Crews, Craig M ^c,d   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Havemayer Hall ^*  (United States)

^c YALE UNIVERSITY   (United States)

^d YALE UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL ACTIVATION; ENAMELS; ENZYME INHIBITION; THERMAL EFFECTS;

AMIDES; PORTEASOME;

SYNTHESIS (CHEMICAL);

ALPHA SILYLALLYL AMIDE; AMIDE; ENAMIDE; ENAMINE; PROPYLAMINE; PROTEASOME INHIBITOR; TMC 95A; TMC 95B; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; HEAT TREATMENT; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMIDES; ANIMALS; CATTLE; CYSTEINE ENDOPEPTIDASES; ERYTHROCYTES; MAGNETIC RESONANCE SPECTROSCOPY; MULTIENZYME COMPLEXES; PEPTIDES, CYCLIC; PIPERIDINES; PROTEASOME ENDOPEPTIDASE COMPLEX; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 2442659012     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja049821k     Document Type: Article

References (40)

1. (a) Rock, K. L.; Gramm, C.; Rothstein, L.; Clark, K.; Stein, R.; Dick, L.; Hwang, D.; Goldberg, A. L. Cell 1994, 78, 761-771.
2. (b) Craiu, A.; Gaczynska, M.; Akopoan, T.; Gramm, C. F.; Fenteany, G.; Gildberg, A.; Rock, K. L. J. Biol. Chem. 1997, 272, 13437-13445.
3. (a) Coux, O.; Tanaka, K.; Goldberg, A. L. Annu. Rev. Biochem. 1996, 65, 801-847.
4. (b) Ciechanover, A. EMBO J. 1998, 17, 7151-7160.
5. Myung, J.; Kim, K. B.; Crews, C. M. Med. Res. Rev. 2001, 21, 245-273.
6. (b) Kisselev, A. F.; Goldberg, A. L. Chem. Biol. 2001, 8, 739-758.
7. (c) Goldberg, A. L.; Rock, K. Nat. Med. 2002, 8, 338-340.
8. Koguchi, Y.; Kohno, J.; Nishio, M.; Takahashi, K.; Okuda, T.; Ohnuki, T. ; Komatsubara, S. J. Antibiot. 2000, 53, 105-109.
9. Kohno, J.; Koguchi, Y.; Nishio, M.; Nakao, K.; Kuroda, M.; Shimizu, R.; Ohnuki, T.; Komatsubara, S. J. Org. Chem. 2000, 65, 990-995.
10. Groll, M.; Koguchi, Y.; Huber, R.; Kohno, J. J. Mol. Biol. 2001, 311, 543-548.
11. (a) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 1967-1970.
12. (b) Inoue, M.; Furyama, H.; Sakazaki, H.; Hirama, M. Org. Lett. 2001, 3, 2863-2865.
13. (c) Ma, D.; Wu, Q. Tetrahedron Lett. 2001, 42, 5279-5281.
14. (d) Albrecht, B. K.; Willians, R. M. Tetrahedron Lett. 2001, 42, 2755-2757.
15. (e) Ma, D.; Wu, Q. Tetrahedron Lett. 2000, 41, 9089-9093.
16. Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2002, 41, 512-515.
17. Albrecht, B. K.; Williams, R. M. Org. Lett. 2003, 5, 197-200.
18. Inoue, M.; Sakazaki, H.; Fukuyama, H.; Hirama, M. Angew. Chem., Int. Ed. 2003, 42, 2654-2657.
19. For a review of Suzuki coupling reactions, see: Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457-2483.
20. McKillop, A.; Taylor, R. K.; Watson, R. J.; Lewis, N. Synthesis 1994, 31-33.
21. Wissner, A.; Brudzinskas, C. V. J. Org. Chem. 1978, 43, 3972-3974.
22. Madin, A.; Overman, L. E. Tetrahedron Lett. 1992, 33, 4859.
23. (a) Marvel, C. S.; Hiers, G. S. Organic Syntheses; Wiley: New York, 1941; Collect. Vol. I, pp 327-330.
24. (b) Lisowski, V.; Robba, M.; Rault, S. J. Org. Chem. 2000, 65, 4193-4194.
25. Crestini, C.; Saladino, R. Synth. Commun. 1994, 24, 2835-2841.
26. Basak, A.; Nayak, M. K.; Chakraboti, A. K. Tetrahedron Lett. 1998, 39, 4883-4886.
27. Sy, W. W. Tetrahedron Lett. 1993, 34, 6223-6224.
28. Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508-7510.
29. Sharpless, K. B.; Amberg, W.; Bennani, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.-S.; Kwong, H.-L.; Morikawa, K.; Wang, Z. M.; Xu, D.; Zhang, X.-L. J. Org. Chem. 1992, 57, 2768-2771.
30. (a) Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361-2364.
31. (b) McKillop, A.; Taylor, R. K.; Watson, R. J.; Lewis, N. Synthesis 1994, 31-33.
32. (a) J. K. Stille, Y. Becker, J. Org, Chem. 1980, 45, 2139-2145.
33. (b) Ribereau, P.; Delamare, M.; Celanire, S.; Queguiner, G. Tetrahedron Lett. 2001, 42, 3571-73.
34. (c) Kuramochi, K.; Watanabe, H.; Kitahara, T. Synlett 2000, 3, 397-399.
35. (d) Chen, R.; Porco, J. A., Jr. Org. Lett. 2000, 2, 1333-1336.
36. Chen, S.-F.; Ho, E.; Mariano, P. S. Tetrahedron 1988, 44, 7013-7026.
37. (a) Bowden, K.; Heibron, I. M.; Jones, E. R. H.; Weedon, B. C. L. J. Chem. Soc. 1946, 39.
38. (b) Pilli, R. A.; Victor, M. M. Tetrahedron Lett. 1998, 39, 4421-4424.
39. Zhang, X. Y.; Houk, K. N.; Lin, S.; Danishefsky, S. J. J. Am. Chem. Soc. 2003, 125, 5111-5114.
40. Yang, Z.-Q.; Kowk, B. H. B.; Lin, S.; Koldobskiy, M. A.; Crews, C. M.; Danishefsky, S. J. ChemBioChem 2003, 4, 508-513.