Stereocontrolled synthesis of the northern part of potent proteasome inhibitor TMC-95A

Organic Letters

Volumn 3, Issue 18, 2001, Pages 2863-2865

  Inoue, Masayuki ^a,b   Furuyama, Hidetomo ^a,b   Sakazaki, Hayato ^a,b   Hirama, Masahiro ^a,b  

^a TOHOKU UNIVERSITY   (Japan)

^b JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPEPTIDE; CYSTEINE PROTEINASE; MULTIENZYME COMPLEX; PROTEASOME; PROTEINASE INHIBITOR; TMC 95A; TMC-95A;

ARTICLE; CHEMISTRY; CONFORMATION; DRUG ANTAGONISM; SYNTHESIS;

CYSTEINE ENDOPEPTIDASES; MOLECULAR CONFORMATION; MULTIENZYME COMPLEXES; PEPTIDES, CYCLIC; PROTEASE INHIBITORS; PROTEASOME ENDOPEPTIDASE COMPLEX;

EID: 0035817973     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol016303v     Document Type: Article

References (39)

1. (a) Kohno, J.; Koguchi, Y.; Nishio, M.; Nakao, K.; Kuroda, M.; Shimizu, R.; Ohnuki, T.; Komatsubara, S. J. Org. Chem. 2000, 65, 990.
2. (b) Koguchi, Y.; Kohno, J.; Nishio, M.; Takahashi, K.; Okuda, T.; Ohnuki, T.; Komatsubara, S. J. Antibiot. 2000, 53, 105.
3. (a) Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113.
4. (b) Fenteany, G.; Schreiber, S. L. J. Biol. Chem. 1998, 273, 8545 and references therein.
5. (a) Hanada, M.; Sugawara, K.; Kaneta, K.; Toda, S.; Nishiyama, Y.; Tomita, K.; Yamamoto, H.; Konishi, M.; Oki, T. J. Antibiot. 1992, 45, 1746.
6. (b) Groll, M.; Kim, K. B.; Kairies, N.; Huber, R.; Crews, C. M. J. Am. Chem. Soc. 2000, 122, 1237 and references therein.
7. TMC-86A, B and TMC-96: (a) Koguchi, Y.; Kohno, J.; Suzuki, S.-i.; Nishio, M.; Takahashi, K.; Ohnuki, T.; Komatsubara, S. J. Antibiot. 1999, 52, 1069.
8. (b) Koguchi, Y.; Kohno, J.; Suzuki, S.-i.; Nishio, M.; Takahashi, K.; Ohnuki, T.; Komatsubara, S. J. Antibiot. 2000, 53, 63. TMC-89A and B:
9. (c) Koguchi, Y.; Nishio, M.; Suzuki, S.-i.; Takahashi, K.; Ohnuki, T.; Komatsubara, S. J. Antibiot. 2000, 53, 967.
10. For a recent review on proteasome inhibitors, see: Myung, J.; Kim, K. B.; Crews, C. M. Med. Res. Rev. 2001, 21, 245.
11. For reviews on the biology of proteasomes, see: (a) Tanaka, K. J. Biochem. 1998, 123, 195.
12. (b) Ciechanover, A. EMBO J. 1998, 17, 7151.
13. Palombella, V. J.; Rando, O. J.; Goldberg, A. L. Maniatis, T. Cell 1994, 78, 773.
14. Rock, K. L.; Gramm, C.; Rothstein, L.; Clark, K.; Stein, R.; Dick, L.; Hwang, D.; Goldberg, A. L. Cell 1994, 78, 761.
15. For synthetic studies on TMC-95 from other laboratories, see: (a) Lin, S.; Danishefsky, S. J. Angew. Chem., Int. Ed. 2001, 40, 1967.
16. (b) Albrecht B. K.; Williams, R. M. Tetrahedron Lett. 2001, 42, 2755.
17. (c) Ma, D.; Wu, Q. Tetrahedron Lett. 2001, 42, 5279.
18. (d) Ma, D.; Wu, Q. Tetrahedron Lett. 2000, 41, 9089.
19. For recent reviews on biaryl synthesis, see: (a) Lloyd-Williams, P.; Giralt, E. Chem. Soc. Rev. 2001, 30, 145.
20. (b) Stanforth, S. P. Tetrahedron 1998, 54, 263.
21. For excellent reviews on Mizoroki-Heck reactions, see: (a) Link, J. T.; Overman, L. E. Intramolecular Heck Reactions in Natural Product Chemistry In Metal-catalyzed Cross-coupling Reactions; Diedrich, F., Stang, P. J.; Eds.; Wiley-VCH Verlag GmbH: Weihheim, 1998; pp 231-269.
22. (b) Beletskaya, I. P.; Cheprakov, A. V. Chem. Rev. 2000, 100, 3009.
23. (c) de Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed. Engl. 1994, 33, 2379.
24. (a) Garner, P.; Park, J. M. J. Org. Chem. 1987, 52, 2361.
25. (b) Garner, P.; Park, J. M. Org. Synth. 1992, 70, 18.
26. The numbering of compounds in this paper corresponds to that of TMC-95A.
27. (a) Lipton, M. F.; Basha, A.; Weinreb, S. M. Org. Synth. 1980, 59, 49.
28. (b) Overman, L. E.; Paone, D. V.; Stearns, B. A. J. Am. Chem. Soc. 1999, 121, 7702.
29. Reaction temperature is crucial for the regioselectivity of this cyclization. For instance, the E/Z ratio of 9 was decreased to 3/1 when the reaction was conducted at 50°C.
30. Madin, A.; Overman, L. E. Tetrahedron Lett. 1992, 33, 4859.
31. While this paper was in preparation, we noticed that Lin and Danishefsky (see ref 9a) planned a similar route to this involving Heck cyclization of a closely related substrate.
32. Macor, J. E.; Ogilvie, R. J.; Wythes, M. J. Tetrahedron Lett. 1996, 37, 4289.
33. Danishefsky, S. J.; Bilodeau, M. T. Angew. Chem., Int. Ed. Engl. 1996, 35, 1380.
34. For a related approach for forming a six-membered carbamate, see: Urabe, H.; Aoyama, Y.; Sato, F. Tetrahedron 1992, 48, 5639.
35. (a) Kobayashi, S.; Reddy, R. S.; Sugiura, Y.; Sasaki, D.; Miyagawa, N.; Hirama, M. J. Am. Chem. Soc. 2001, 123, 2887.
36. (b) Holcombe, J. L.; Livinghouse, T. J. Org. Chem. 1986, 51, 111.
37. Zhao, M.; Li, J.; Song, Z.; Desmond, R.; Tschaen, D. M.; Grabowski, E. J. J.; Reider, P. J. Tetrahedron Lett. 1998, 39, 5323.
38. Pansare, S. V.; Vederas, J. C. J. Org. Chem. 1989, 54, 2311.
39. +] 500.0457, found 500.0433.