A concise route to (+)-lactacystin

Journal of Organic Chemistry

Volumn 69, Issue 22, 2004, Pages 7765-7768

  Ooi, Hidenori ^a   Ishibashi, Norihisa ^a   Iwabuchi, Yoshiharu ^a   Ishihara, Jun ^a   Hatakeyama, Susumi ^a  

^a NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CHROMATOGRAPHIC ANALYSIS; PROPANE; SYNTHESIS (CHEMICAL);

(+)-LACTACYSTIN; ASYMMETRIC CROTYLATION; FACILE CHROMATOGRAPHY; PROTEASOME INHIBITORS;

ENZYME INHIBITION;

2 AMINO 2 (HYDROXYMETHYL)PROPANE 1,3 DIOL; CARBAMIC ACID DERIVATIVE; LACTACYSTIN; LACTACYSTIN BETA LACTONE; PROPANE; PROTEASOME INHIBITOR; TERT BUTYL 5 FORMYL 2,2 DIMETHYL 1,3 DIOXAN 5 YLCARBAMATE; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; ESTERIFICATION; METHANOLYSIS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REDUCTION; REPRODUCIBILITY; ROOM TEMPERATURE; STEREOCHEMISTRY; TECHNIQUE;

ACETYLCYSTEINE; CARBAMATES; CATALYSIS; MOLECULAR STRUCTURE; PROTEASOME ENDOPEPTIDASE COMPLEX; STEREOISOMERISM; TROMETHAMINE;

EID: 6344221776     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo048817o     Document Type: Article

References (33)

1. Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113-116.
2. (b) Omura, S.; Natsuzaki, K.; Fujimoto, T.; Kosuge, K.; Furuya, T.; Fujita, S.; Nakagawa, A. J. Antibiot. 1991, 44, 117-118.
3. Fenteany, G.; Standaert, R. F.; Reichard, G. A.; Corey, E. J.; Schreiber, S. L. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 3358-3362.
4. (b) Fenteany, G.; Standaert, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.; Schreiber, S. L. Science 1995, 268, 726-731.
5. (c) Dick, L. R.; Cruikshank, A. A.; Grenier, L.; Melandri, F. D.; Nunes, S. L.; Stein, R. L. J. Biol. Chem. 1996, 277, 7273-7275.
6. (d) Adams, J. A.; Stein, R. Ann. Rep. Med. Chem. 1996, 31, 279-288.
7. (e) Groll, M.; Ditzel, L.; Löwe, J.; Stock, D.; Bochtler, M.; Bartunik, H. D.; Huber, R. Nature 1997, 386, 463-471.
8. (f) Dick, L. R.; Cruikshank, A. A.; Destree, A. T.; Grenier, L.; McCormack, T. A.; Melandri, F. D.; Nunes, S. L.; Palombella, V. J.; Parent, L. A.; Plamondon, L.; Stein, R. L. J. Biol. Chem. 1997, 272, 182.
9. DeMartino, G. N.; Slaughter, C. A. J. Biol. Chem. 1999, 274, 22123-22126.
10. (a) Conner, E. M.; Brand, S.; Davis, J. M.; Laroux, F. S.; Palombella, V. J.; Fuseler, J. W.; Kang, D. Y.; Wolf, R. E.; Grisham, M. B. J. Pharm. Exp. Therap. 1997, 282, 1615-1622.
11. (b) Soucy, F.; Grenier, L.; Behnke, M. L.; Destree, A. T.; McCormack, T. A.; Adams, J.; Plamondon, L. J. Am. Chem. Soc. 1999, 121, 9967-9976 and references therein.
12. For reviews on synthetic efforts towards lactacystin, see: (a) Corey, E. J.; Li, W.-D. Z. Chem. Pharm. Bull. 1999, 47, 1-10.
13. (b) Masse, C. E.; Morgan, A. J.; Adams, J.; Panek, J. S. Eur. J. Org. Chem. 2000, 2513-2528.
14. (a) Iwama, S.; Gao, W.-G.; Shinada, T. Ohfune, Y. Synlett 2000, 1631-1633.
15. (b) Care, S. N.; Corey, E. J. Org. Lett. 2001, 3, 1395-1397.
16. (c) Cook, G. R.; Shanker, P. S. J. Org. Chem. 2001, 66, 6818-6822.
17. (d) Green, M. P.; Prodger, J. C.; Hayes, C. J. Tetrahedron Lett. 2002, 43, 6609-6611.
18. (e) Page, P. C. B.; Leach, D. C.; Hayman, C. M.; Hamzah, A. S.; Allin, S. M.; McKee, V. Synlett 2003, 1025-1027.
19. (f) Page, P. C. B.; Hamzah, A. S.; Leach, D. C.; Allin, S. M.; Andrews, D. M.; Rassias, G. A. Org. Lett. 2003, 5, 353-355.
20. (g) Brennan, C. J.; Pattenden, G.; Rescourio, G. Tetrahedron Lett. 2003, 44, 8757-8760.
21. (h) Donohoe, T. J.; Sintim, H. O.; Sisangia, L.; Harling, J. D. Angew. Chem., Int. Ed. 2004, 43, 2293-2296.
22. Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677-10678.
23. Kang, S. H.; Jun, H.-S. Chem. Commun. 1998, 1929-1930.
24. Uno, H.; Baldwin, J. E.; Russell, A. T. J. Am. Chem. Soc. 1994, 776, 2139-2140.
25. (a) Roush, W. R.; Halterman, R. L. J. Am. Chem. Soc. 1986, 108, 3422-3434.
26. (b) Roush, W. R.; Ando, K.; Powers, D. B.; Palkowitz, A. D.; Halterman, R. L. J. Am. Chem. Soc. 1990, 772, 6339-6348.
27. (a) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 293-294.
28. (b) Brown, H. C.; Bhat, K. S. J. Am. Chem. Soc. 1986, 108, 5919-5923.
29. When PCC was used in place of PDC, the α,β-unsaturated lactam, a dehydration product of 15, was also obtained in 19% yield along with 15 (46%).
30. Griffith, W. P.; Ley, S. V.; Whitcombe, G. P.; White, A. D. J. Chem. Soc., Chem. Commun. 1987, 1625-1627.
31. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc., 1991, 113, 7277-7287.
32. (a) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B., III. J. Am. Chem. Soc. 1998, 118, 3584-3590.
33. (b) Corey, E. J.; Li, W.; Reichard, G. A. J. Am. Chem. Soc. 1998, 120, 2330-2336.