An enantioselective formal synthesis of (+)-lactacystin from hydroxymethyl glutamic acid (HMG)

Synlett

Volumn , Issue 4, 2010, Pages 535-538

  Hameed, Abdul ^a   Blake, Alexander J ^a   Hayes, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Alkylidene carbene; CH insertion; Hydroxymethyl glutamic acid; Lactacystin

Indexed keywords

GLUTAMIC ACID; HYDROXYMETHYL GLUTAMIC ACID; LACTACYSTIN; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ENANTIOSELECTIVITY; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 77955362851     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219207     Document Type: Article

References (44)

1. Omura, S.; Fujimoto, T.; Otoguro, K.; Matsuzaki, K.; Moriguchi, R.; Tanaka, H.; Sasaki, Y. J. Antibiot. 1991, 44, 113.
2. Fenteany, G.; Standaert, R. F.; Lane, W. S.; Choi, S.; Corey, E. J.; Schreiber, S. L. Science 1995, 268, 726.
3. (a) Pattenden, G.; Rescourio, G. Org. Biomol. Chem. 2008, 6, 3428.
4. (b) Legeay, J.-C.; Langlois, N. J. Org. Chem. 2007, 72, 10108.
5. (c) Yoon, C. H.; Flanigan, D. L.; Yoo, K. S.; Jung, K. W. Eur. J. Org. Chem. 2007, 37.
6. (d) Gilley, C. B.; Buller, M. J.; Kobayashi, Y. Org. Lett. 2007, 9, 3631.
7. (e) Balskus, E. P.; Jacobsen, E. N. J. Am. Chem. Soc. 2006, 128, 6810.
8. (f) Wardrop, D. J.; Bowen, E. G. Chem. Commun. 2005, 5106.
9. (g) Ooi, H.; Ishibashi, N.; Iwabuchi, Y.; Ishihara, J.; Hatekeyama, S. J. Org. Chem. 2004, 69, 7765.
10. (h) Brennan, C. J.; Pattenden, G.; Rescourio, G. Tetrahedron Lett. 2003, 44, 8757.
11. (i) Green, M. P.; Prodger, J. C.; Hayes, C. J. Tetrahedron Lett. 2002, 43, 6609.
12. (j) Iwama, S.; Gao, W. G.; Shinada, T.; Ohfune, Y. Synlett 2000, 1631.
13. (k) Panek, J. S.; Masse, C. E. Angew. Chem. Int. Ed. 1999, 38, 1093.
14. (l) Kang, S. H.; Jun, H. S.; Youn, J. H. Synlett 1998, 1045.
15. (m) Corey, E. J.; Li, W. D.; Reichard, G. A. J. Am. Chem. Soc. 1998, 120, 2330.
16. (n) Corey, E. J.; Li, W. D.; Nagamitsu, T. Angew. Chem. Int. Ed. 1998, 37, 1676.
17. (o) Chida, N.; Takeoka, J.; Ando, K.; Tsutsumi, N.; Ogawa, S. Tetrahedron 1997, 53, 16287.
18. (p) Nagamitsu, T.; Sunazuka, T.; Tanaka, H.; Omura, S.; Sprengeler, P. A.; Smith, A. B. J. Am. Chem. Soc. 1996, 118, 3584.
19. (q) Chida, N.; Takeoka, J.; Tsutsumi, N.; Ogawa, S. J. Chem. Soc., Chem. Commun. 1995, 793.
20. (r) Uno, H.; Baldwin, J. E.; Russell, A. T. J. Am. Chem. Soc. 1994, 116, 2139.
21. (s) Sunazuka, T.; Nagamitsu, T.; Matsuzaki, K.; Tanaka, H.; Omura, S.; Smith, A. B. J. Am. Chem. Soc. 1993, 115, 5302.
22. (t) Corey, E. J.; Reichard, G. A.; Kania, R. Tetrahedron Lett. 1993, 34, 6977.
23. (u) Corey, E. J.; Reichard, G. A. J. Am. Chem. Soc. 1992, 114, 10677.
24. (a) Hayes, C. J.; Sherlock, A. E.; Green, M. P.; Wilson, C.; Blake, A. J.; Selby, M. D.; Prodger, J. C. J. Org. Chem. 2008, 73, 2041.
25. (b) Hayes, C. J.; Sherlock, A. E.; Selby, M. D. Org. Biomol. Chem. 2006, 4, 193.
26. (a) Donohoe, T. J.; Sintim, H. O.; Sisangia, L.; Ace, K. W.; Guyo, P. M.; Cowley, A.; Harling, J. D. Chem. Eur. J. 2005, 11, 4227.
27. (b) Donohoe, T. J.; Sintim, H. O.; Sisangia, L.; Harling, J. D. Angew. Chem. Int. Ed. 2004, 43, 2293.
28. Fukuda, N.; Sasaki, K.; Sastry, T. V. R. S.; Kanai, M.; Shibasaki, M. J. Org. Chem. 2006, 71, 1220.
29. An independent route to lactam 3 has been reported previously en route to (-)-kaitocephaline, see: Kawasaki, M.; Shinada, T.; Hamda, M.; Ohfune, Y. Org. Lett. 2005, 7, 4165.
30. (a) Zhang, J.; Flippen-Anderson, J. L.; Kozikowski, A. P. J. Org. Chem. 2001, 66, 7555.
31. (b) Choudhury, P. K.; Le Nguyen, B. K.; Langlois, N. Tetrahedron Lett. 2002, 43, 463.
32. (c) Langlois, N.; Le Nguyen, B. K. J. Org. Chem. 2004, 69, 7558.
33. (d) Kawasaki, M.; Namba, K.; Tsujishima, H.; Shinada, T.; Ohfune, Y. Tetrahedron Lett. 2003, 44, 1235.
34. (e) Lee, J.; Lee, Y.-I.; Kang, M. J.; Lee, Y.-J.; Jeong, B.-S.; Lee, J.-H.; Kim, M.-J.; Choi, J.-Y.; Ku, J.-M.; Park, H.-G.; Jew, S.-S. J. Org. Chem. 2005, 70, 4158.
35. (f) Lee, Y.-J.; Lee, J.; Kim, M.-J.; Jeong, B.-S.; Lee, J.-H.; Kim, T.-S.; Lee, J.; Ku, J.-M.; Jew, S.-S.; Park, H.-G. Org. Lett. 2005, 7, 3207.
36. (g) Battistini, L.; Curti, C.; Zanardi, F.; Rassu, G.; Auzzas, L.; Casiraghi, G. J. Org. Chem. 2004, 69, 2611.
37. (h) Tang, G.; Tian, H.; Ma, D. Tetrahedron 2004, 60, 10547.
38. Hayes, C. J.; Bradley, D. M.; Thomson, N. M. J. Org. Chem. 2006, 71, 2661.
39. Welch, S. C.; Chou, C. Y.; Gruber, J. M.; Assercq, J. M. J. Org. Chem. 1985, 50, 2668.
40. CCDC 753698 and 753699 contain the supplementary crystallographic data for this paper (for 19 and 20). These data can be obtained free of charge from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/ cif.
41. Kang, S. H.; Jun, H. S. Chem. Commun. 1998, 1929.
42. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1983, 48, 4155.
43. Corey, E. J.; Li, W. D.; Nagamitsu, T. Angew. Chem. Int. Ed. 1998, 37, 1676.
44. Andrews, D. M.; Brewster, A. G.; Moloney, M. G. J. Chem. Soc., Perkin Trans. 1 2002, 80.