A formal synthesis of (+)-lactacystin from 4-hydroxyproline

Tetrahedron Letters

Volumn 54, Issue 1, 2013, Pages 55-57

  Mycock, David K ^a   Glossop, Paul A ^b   Lewis, William ^a   Hayes, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

Author keywords

(+) Lactacystin; Diastereoselective; Enolate acylation; Quaternary stereogenic centre; trans Hydroxyproline

Indexed keywords

3 PYRROLINE; 3 PYRROLINONE; CARBON; CARBONIC ACID; DEXTRO LACTACYSTIN; HYDROXYPROLINE; LACTACYSTIN; PYRROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CHEMICAL STRUCTURE; DEHYDRATION REACTION; DEPROTECTION REACTION; DIASTEREOISOMER; HYDROGENATION; OXIDATION; SYNTHESIS;

EID: 84870300220     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.10.076     Document Type: Article

References (44)

1. S. Õmura, T. Fujimoto, K. Otoguro, K. Matsuzaki, R. Moriguchi, H. Tanaka, and Y. Sasaki J. Antibiot. 44 1991 113
2. G. Fenteany, R.F. Standaert, W.S. Lane, S. Choi, E.J. Corey, and S.L. Schreiber Science 268 1995 726
3. W. Gu, and R.B. Silverman J. Org. Chem. 76 2011 8287
4. A. Hameed, A.J. Blake, and C.J. Hayes Synlett 2010 535
5. C.J. Hayes, A.E. Sherlock, M.P. Green, C. Wilson, A.J. Blake, M.D. Selby, and J.C. Prodger J. Org. Chem. 73 2008 2041
6. G. Pattenden, and G. Rescourio Org. Biomol. Chem. 6 2008 3428
7. H. Miyaoka, M. Yamanishi, A. Hoshino, H. Mitome, and E. Kawashima Chem. Pharm. Bull. 56 2008 738
8. J.-C. Legeay, and N. Langlois J. Org. Chem. 72 2007 10108
9. C.H. Yoon, D.L. Flanigan, K.S. Yoo, and K.W. Jung Eur. J. Org. Chem. 2007 37
10. C.B. Gilley, M.J. Buller, and Y. Kobayashi Org. Lett. 9 2007 3631
11. M. Shibasaki, M. Kanai, and N. Fukuda Chem. Asian J. 2 2007 20
12. N. Fukuda, K. Sasaki, T.V.R.S. Sastry, M. Kanai, and M. Shibasaki J. Org. Chem. 7 2006 4165
13. C.J. Hayes, A.E. Sherlock, and M.D. Selby Org. Biomol. Chem. 4 2006 193
14. E.P. Balskus, and E.N. Jacobsen J. Am. Chem. Soc. 128 2006 6810
15. D.J. Wardrop, and E.G. Bowen Chem. Commun. 2005 5106
16. T.J. Donohoe, H.O. Sintim, L. Sisangia, K.W. Ace, P.M. Guyo, A. Cowley, and J.D. Harling Chem. Eur. J. 11 2005 4227
17. T.J. Donohoe, H.O. Sintim, L. Sisangia, and J.D. Harling Angew. Chem., Int. Ed. 43 2004 2293
18. H. Ooi, N. Ishibashi, Y. Iwabuchi, J. Ishihara, and S. Hatekeyama J. Org. Chem. 69 2004 7765
19. C.J. Brennan, G. Pattenden, and G. Rescourio Tetrahedron Lett. 44 2003 8757
20. M.P. Green, J.C. Prodger, and C.J. Hayes Tetrahedron Lett. 43 2002 6609
21. S. Iwama, W.G. Gao, T. Shinada, and Y. Ohfune Synlett 2000 1631
22. J.S. Panek, and C.E. Masse Angew. Chem., Int. Ed. 38 1999 1093
23. S.H. Kang, H.S. Jun, and J.H. Youn Synlett 1998 1045
24. E.J. Corey, W.D. Li, and G.A. Reichard J. Am. Chem. Soc. 120 1998 2330
25. E.J. Corey, W.D. Li, and T. Nagamitsu Angew. Chem., Int. Ed. 37 1998 1676
26. N. Chida, J. Takeoka, K. Ando, N. Tsutsumi, and S. Ogawa Tetrahedron 53 1997 16287
27. T. Nagamitsu, T. Sunazuka, H. Tanaka, S. Omura, P.A. Sprengeler, and A.B. Smith J. Am. Chem. Soc. 118 1996 3584
28. N. Chida, J. Takeoka, N. Tsutsumi, and S. Ogawa J. Chem. Soc., Chem. Commun. 1995 793
29. H. Uno, J.E. Baldwin, and A.T. Russell J. Am. Chem. Soc. 116 1994 2139
30. T. Sunazuka, T. Nagamitsu, K. Matsuzaki, H. Tanaka, S. Omura, and A.B. Smith J. Am. Chem. Soc. 115 1993 5302
31. E.J. Corey, G.A. Reichard, and R. Kania Tetrahedron Lett. 34 1993 6977
32. E.J. Corey, and G.A. Reichard J. Am. Chem. Soc. 114 1992 10677
33. R.G. Vaswani, and A.R. Chamberlin J. Org. Chem. 73 2008 1661
34. R.G. Vaswani, A. Limon, J.M. Reyes-Ruiz, R. Miledi, and A.R. Chamberlin Bioorg. Med. Chem. Lett. 19 2009 132
35. T. Honda, and C. Hisa Heterocycles 80 2010 1381
36. R. Filosa, C. Holder, and Y.P. Auberson Tetrahedron Lett. 47 2006 8929
37. O. Tamura, T. Yanagimachi, and H. Ishibashi Tetrahedron: Asymmetry 14 2003 3033
38. S. Nagumo, A. Matoba, Y. Ishii, S. Yamaguchi, N. Akutsu, H. Nishijima, A. Nishida, and N. Kawahara Tetrahedron 58 2002 9871
39. J. Cossy, O. Mirguet, and D. Gomez Pardo Synlett 2001 1575
40. S. Nagumo, M. Mizukami, N. Akutsu, A. Nishida, and N. Kawahara Tetrahedron Lett. 40 1999 3209
41. T. Sato, Y. Kugo, E. Nakaumi, H. Ishibashi, and M. Ikeda J. Chem. Soc., Perkin Trans. 1 1995 1801
42. D. Ma, and J. Yang J. Am. Chem. Soc. 123 2001 9706
43. See conversion of compound SI-66 into compound 2 in the Supplementary data of the following Letter: M. Brichacek, D. Lee, and J.T. Njardarson Org. Lett. 10 2008 5023
44. M. Oba, C. Ito, T. Hayashi, and K. Nishiyama Tetrahedron Lett. 50 2009 5053