An efficient, stereocontrolled synthesis of a potent omuralide-salinosporin hybrid for selective proteasome inhibition

Journal of the American Chemical Society

Volumn 127, Issue 25, 2005, Pages 8974-8976

  Reddy, Leleti Rajender ^a   Fournier, Jean François ^a   Reddy, B V Subba ^a   Corey, E J ^a  

^a HARVARD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTACYSTIN BETA LACTONE; PROTEASOME INHIBITOR; SALINOSPORAMIDE A; SALINOSPORIN; UNCLASSIFIED DRUG;

ACIDIFICATION; ARTICLE; BAYLIS HILLMAN REACTION; CRYSTALLIZATION; CYCLIZATION; DESILYLATION; DIASTEREOISOMER; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY; SWERN OXIDATION; X RAY CRYSTALLOGRAPHY;

ENZYME INHIBITORS; LACTONES; MOLECULAR CONFORMATION; PROTEASOME ENDOPEPTIDASE COMPLEX; PYRROLES; STEREOISOMERISM;

EID: 21244463812     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja052376o     Document Type: Article

References (31)

1. Reviewed in: (a) Corey, E. J.; Li, W.-D. Z. Chem. Pharm. Bull. 1999, 47, 1-10.
2. (b) Corey, E. J.; Reichard, G. A.; Kania, R. Tetrahedron Lett. 1993, 34, 6977-6980.
3. (c) Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677-10678.
4. (d) Corey, E. J.; Li, W.; Reichard, G. A. J. Am. Chem. Soc. 1998, 120, 2330-2336.
5. (e) 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.
6. (f) Fenteany, G.; Standaert, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.; Schreiber, S. L. Science 1995, 268, 726-731.
7. (a) Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113-116.
8. (b) Omura, S.; Matsuzaki, K.; Fujimoto, T.; Kosuge, K.; Furuya, T.; Fujita, S.; Nakagawa, A. J. Antibiot. 1991, 44, 117-118.
9. Bortezomib (Velcade), a peptidyl boronic acid which is a reversible (0.6 nM Ki) proteasome inhibitor, is currently in use and approved for the treatment of multiple myeloma. In addition, there are numerous ongoing clinical trials on the use of this agent for treatment of other malignant diseases. See: (a) Richardson, P. G. et al. N. Engl. J. Med. 2003, 348, 2609-2617.
10. (b) Richardson, P. G.; Hideshima, T.; Anderson, K. C. Cancer Control 2003, 10, 361-369.
11. (c) Steinberg, D. The Scientist 2003, 17 (S2), S18-S22.
12. (d) Adams, J. Proteasome Inhibitors in Cancer Therapy; Humana Press: New York, 2004.
13. Feling, R. H.; Buchanan, G. O.; Mincer, T. J.; Kauffman, C. A.; Jensen, P. R.; Fenical, W. Angew. Chem., Int. Ed. 2003, 42, 355-357.
14. Reddy, L. R.; Saravanan, P.; Corey, E. J. J. Am. Chem. Soc. 2004, 126, 6230-6231.
15. For reviews on applications of titanacyclopropane reagents, see: (a) Kulinkovich, O. G. Chem. Rev. 2003, 103, 2597-2632.
16. (b) Sato, F.; Okamoto, S. Adv. Synth. Catal. 2001, 343, 759-784.
17. For the closest precedent to this cyclization involving δ,ε-enones. see: (a) Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 3182-3191.
18. (b) Mandal, S. K.; Amin, S. R.; Crowe, W. E. J. Am. Chem. Soc. 2001, 123, 6457-6458.
19. (c) Crowe, W. E.; Vu, A. T. J. Am. Chem. Soc. 1996, 118, 1557-1558.
20. (d) Quan, L. G.; Cha, J. K. Tetrahedron Lett. 2001, 42, 8567-8569.
21. For a detailed study of the pathway for the stereochemistry of the conversion of 7 to 8, see: Reddy, L. R.; Fournier, J.-F.; Subba Reddy, B. V.; Corey, E. J. Org. Lett. ASAP.
22. 2, see: (a) Sibi, M. P.; He, L. Org. Lett. 2004, 6, 1749-1752.
23. (b) Kim, K.; Okamoto, S.; Sato, F. Org. Lett. 2001, 3, 67-69.
24. For reviews, see: (a) Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 3rd ed.; John Wiley & Sons: New York, 1999.
25. (b) Kocienski, P. J. Protecting Croups, 3rd ed.: Georg Thieme: Stuttgart, New York, 2004.
26. (c) Salomon, C. J.; Mata, E. G.; Mascaretti, O. A. Tetrahedron 1993, 49, 3691-3734.
27. (d) Nicolaou, K. C.; Estrada, A. A.; Zak, M.; Lee, S. H.; Safina, B. S. Angew. Chem., Int. Ed. 2005, 44, 1378-1382.
28. (e) Olah, G. A.; Narang, S. C.; Salem, G. F.; Gupta, B. G. B. Sythesis 1981, 142-143.
29. (f) Marchand, P. S. J. Chem. Soc., Chem. Commun. 1971, 667-668.
30. (g) Bartlett, P. A.; Johnson, W. S. Tetrahedron Lett. 1970, 4459-4462.
31. Because of the availability of the hybrid molecule 3 by the synthetic route that is summarized in Scheme 1 and also because of its likely irreversible mode of action in vivo, we assign it the name "antiprotealide" in the expectation that it represents a convenient and useful tool in experimental biology and medicine. For a recent review of natural product hybrids, see: Tietze, L. F.; Bell, H. P.; Chandrasekhar, S. Angew. Chem., Int. Ed. 2003, 42, 3996-4028.