Syntheses and biological evaluation of (+)-lactacystin and analogs

European Journal of Organic Chemistry

Volumn , Issue 14, 2000, Pages 2513-2528

  Masse, Craig E ^a   Morgan, Adam J ^a   Adams, Julian ^b   Panek, James S ^a  

^a BOSTON UNIVERSITY   (United States)

^b MILLENNIUM PHARMACEUTICALS INC   (United States)

Author keywords

Aminohydroxylation; Asymmetric synthesis; Lactacystin; Natural products; Proteasome inhibitor; Structure activity relationship

Indexed keywords

LACTACYSTIN; PROTEINASE INHIBITOR;

ENZYME INHIBITOR INTERACTION; PROTEINASE INHIBITION; REACTION ANALYSIS; SHORT SURVEY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033859279     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200007)2000:14<2513::AID-EJOC2513>3.0.CO;2-D     Document Type: Short Survey

References (56)

1. S. Omura, T. Fujimoto, K. Otoguro, K. Matsuzaki, R. Moriguchi, H. Tanaka, Y. Sasaki, J. Antibiot. 1991, 44, 113-116.
2. S. Omura, K. Matsuzaki, T. Fujimoto, K. Kosuge, T. Furuya, S. Fujita, A. Nakagawa, J. Antibiot. 1991, 44, 117-118.
3. [3a] G. Fenteany, R. F. Standaert, G. A. Reichard, E. J. Corey, S. L. Schreiber, Proc. Natl. Acad. Sci., USA 1994, 91, 3358-3362.
4. [3b] G. Fenteany, R. F. Standaert, W. S. Lane, S. Choi, E. J. Corey, S. L. Schreiber, Science 1995, 268, 726-731.
5. G. N. DeMartino, C. A. Slaughter, J. Biol. Chem. 1999, 274, 22123-22126.
6. [5a] P. Elliott, C. Pien, I. Chapman, J. Adams, J. Allergy Clin. Imuun. 1999, 104, 1-7.
7. [5b] B. Campbell, J. Adams, Y. K. Shin, A. M. Lefer, J. Molec. Cell. Cardio. 1999, 31, 467-476.
8. [5c] J. Adams, V. J. Palombella, E. A. Sausville, J. Johnson, A. Destree, D. D. Lazarus, J. Cancer Res. 1999, 59, 2615-2622.
9. [5d] M. B. Grisham, V. J. Palombella, P. J. Elliott, E. M. Connor, S. Brand, H. L. Wong, C. Pien, L. M. Mazolla, A. Destree, L. Parent, J. Adams, Meth. in Enzym. 1999, 300, 345-363.
10. [5e] B. Teicher, G. Ara, R. Herbst, V. Palombella, J. Adams, Clin. Cancer Res. 1999, 5, 2638-2645.
11. M. Groll, L. Ditzel, J. Löwe, D. Stock, M. Bochtler, H. D. Bartunik, R. Huber, Nature 1997, 386, 463-471.
12. [7a] L. R. Dick, A. A. Cruikshank, L. Grenier, F. D. Melandri, S. L. Nunes, R. L. Stein, J. Biol. Chem. 1996, 271, 7273-7275.
13. [7b] J. A. Adams, R. Stein, Ann. Rep. Med. Chem. 1996, 31, 279-288.
14. For an earlier review on synthetic efforts towards (+)-lactacystin see: E. J. Corey, W.-D. Z. Li, Chem. Pharm. Bull. 47, 1999, 1-10.
15. J. S. Panek, C. E. Masse, Angew. Chem. Int. Ed. 1999, 38, 1093-1095.
16. J. S. Panek, C. E. Masse, J. Org. Chem. 1998, 63, 2382-2384.
17. A. Shanzer, L. Somekh, D. Butina, J. Org. Chem. 1979, 44, 3967-3969.
18. [12a] J. T. B. H. Jastrzebski, G. van Koten, W. F. van de Mieroop, Inorg. Chim. Acta. 1988, 142, 169-171.
19. [12b] F. H. van der Steen, H. Kleijn, J. T. B. H. Jastrzebski, G. van Koten, J. Org. Chem. 1991, 56, 5147-5158.
20. [13a] G. Li, H.-T. Chang, K. B. Sharpless, Angew. Chem. Int. Ed. Engl. 1996, 35, 451-454.
21. [13b] B. Tao, G. Schlingloff, K. B. Sharpless, Tetrahedron Lett. 1998, 39, 2507-2510.
22. H. Han, C.-W. Cho, K. D. Janda, Chem. Eur. J. 1999, 5, 1565-1569.
23. A. J. Morgan, C. E. Masse, J. S. Panek Org. Lett. 1999, 1, 1949-1953.
24. L. P. Hammett, J. Am. Chem. Soc. 1937, 59, 96-99. For a similar type of analysis see: M. Palucki, N. S. Finney, P. J. Pospisil, M. L. Guler, T. Ishida, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 948-954.
25. L. P. Hammett, J. Am. Chem. Soc. 1937, 59, 96-99. For a similar type of analysis see: M. Palucki, N. S. Finney, P. J. Pospisil, M. L. Guler, T. Ishida, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 948-954.
26. Molecular modeling studies with substrate 9 (Chem 3D Pro, MM2 minimization) indicate the internuclear distance between H1 and H4 to be ca. 3.0 Å.
27. K. B. Wiberg, K. E. Laidig, J. Am. Chem. Soc. 1987, 109, 5935-5943.
28. For precedent relative to the formation of such aryl-osmium π-complexes see: J. M. Wallace, J. K. Kochi, J. Org. Chem. 1988, 53, 1679-1686.
29. T. Sunazuka, T. Nagamitsu, K. Matsuzaki, H. Tanaka, S. Omura, A. B. Smith III, J. Am. Chem. Soc. 1993, 115, 5302-5304.
30. S. Masamune, W. Choy, J. S. Peterson, L. R. Sita, Angew. Chem. 1985, 97, 1-31. ; Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30.
31. S. Masamune, W. Choy, J. S. Peterson, L. R. Sita, Angew. Chem. 1985, 97, 1-31. ; Angew. Chem. Int. Ed. Engl. 1985, 24, 1-30.
32. For related bond constructions of the silane reagents with oxazoles see: P. Liu, J. S. Panek, Tetrahedron Lett. 1998, 39, 6143-6146.
33. E. J. Corey, W. Li, G. A. Reichard, J. Am. Chem. Soc. 1998, 120, 2330-2336.
34. For the preparation of the silane reagents see: R. T. Beresis, J. S. Solomon, M. G. Yang, N. F. Jain, J. S. Panek, Org. Synth. 1997, 78-88. For a review on the use of the chiral (E)-crotylsilane reagents see: C. E. Masse, J. S. Panek, Chem. Rev. 1995, 95, 1293-1316.
35. For the preparation of the silane reagents see: R. T. Beresis, J. S. Solomon, M. G. Yang, N. F. Jain, J. S. Panek, Org. Synth. 1997, 78-88. For a review on the use of the chiral (E)-crotylsilane reagents see: C. E. Masse, J. S. Panek, Chem. Rev. 1995, 95, 1293-1316.
36. F. Soucy, L. Grenier, M. L. Behnke, A. T. Destree, T. A. McCormack, J. Adams, L. Plamondon, J. Am. Chem. Soc. 1999, 121, 9967-9976.
37. [26a] H.-P. Wessel, T. Iversen, D. R. Bundle, J. Chem. Soc., Perkin Trans. 1 1985, 2247-2250.
38. [26b] U. Widmer, Synthesis 1987, 568-570.
39. E. J. Corey, G. A. Reichard, J. Am. Chem. Soc. 1992, 114, 10677-10678.
40. M. C. Pirrung, C. H. Heathcock, J. Org. Chem. 1980, 45, 1727-1728.
41. E. J. Corey, A. G. Myers, J. Am. Chem. Soc. 1985, 707, 5574-5576.
42. [30a] E. J. Corey, W. Li, T. Nagamitsu, Angew. Chem. Int. Ed. 1998, 37, 1676-1679.
43. [30b] E. J. Corey, W-D. Z. Li, Tetrahedron 1999, 55, 3305-3316.
44. E. J. Corey, W-D. Li, Tetrahedron Lett. 1998, 39, 7475-7478.
45. [32a] E. J. Corey, G. A. Reichard, Tetrahedron Lett. 1993, 34, 6973-6976.
46. [32b] E. J. Corey, W-D. Z. Li, Tetrahedron Lett. 1998, 39, 8043-8046.
47. E. J. Corey, S. Choi, Tetrahedron Lett. 1993, 34, 6969-6972.
48. E. J. Corey, D.-H. Lee, S. Choi, Tetrahedron Lett. 1992, 33, 6735-6738.
49. T. Nagamitsu, T. Sunazuka, H. Tanaka, S. Omura, P. A. Sprengeler, A. B. Smith III, J. Am. Chem. Soc. 1996, 118, 3584-3590.
50. [36a] H. C. Brown, K. S. Bhat, J. Am. Chem. Soc. 1986, 108, 293-294.
51. [36b] H. C. Brown, K. S. Bhat, J. Am. Chem. Soc. 1986, 108, 5919-5923.
52. Y. Okuda, S. Hirano, T. Hiyama, H. Nozaki, J. Am. Chem. Soc. 1977, 99, 3179-3181.
53. W. R. Roush, M. A. Adam, A. E. Walts, D. J. Harris, J. Am. Chem. Soc. 1986, 108, 3422-3434.
54. W. R. Roush, K. Ando, D. B. Powers, A. D. Palkowitz, R. L. Halterman, J. Am. Chem. Soc. 1990, 112, 6339-6348.
55. H. Uno, J. E. Baldwin, A. T. Russell, J. Am. Chem. Soc. 1994, 116, 2139-2140.
56. N. Chida, J. Takeoka, N. Tsutsumi, S. Ogawa, J. Chem. Soc., Chem. Commun. 1995, 793-794.