Synthesis of non-proteinogenic amino acids using Michael addition to unsaturated orthopyroglutamate derivative

Tetrahedron

Volumn 65, Issue 1, 2009, Pages 128-133

  Oba, Makoto ^a   Saegusa, Tsuneki ^a   Nishiyama, Naohiro ^a   Nishiyama, Kozaburo ^a  

^a TOKAI UNIVERSITY   (Japan)

Author keywords

ABO ester; Amino acids; Michael addition; Pyroglutaminol

Indexed keywords

AMINO ACID DERIVATIVE; BACLOFEN; GLUTAMIC ACID DERIVATIVE; METHYL 3 (4 CHLOROPHENYL)PYROGLUTAMATE; METHYL N BENZYL 3 (4 CHLOROPHENYL)PYROGLUTAMATE; METHYL N TERT BUTOXYCARBONYL 3 (4 CHLOROPHENYL)PYROGLUTAMATE; METHYL N TERT BUTOXYCARBONYL 3 [BIS(ETHOXYCARBONYL)METHYL]PYROGLUTAMATE; METHYL N TERT BUTOXYCARBONYL 3 METHYLPYROGLUTAMATE; METHYL N TERT BUTOXYCARBONYL 3 PHENYLPYROGLUTAMATE; PYROGLUTAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBOXY TERMINAL SEQUENCE; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; MICHAEL ADDITION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 56949087464     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.10.092     Document Type: Article

References (46)

1. Reviews:
2. Haldar D. Curr. Org. Synth. 5 (2008) 61-80
3. Perdih A., and Dolenc M.S. Curr. Org. Chem. 11 (2007) 801-832
4. Galeazzi R., Mobbili G., and Orena M. Curr. Org. Chem. 8 (2004) 1799-1829
5. Coppola G.M., and Schuster H.F. Asymmetric Synthesis. Construction of Chiral Molecule Using Amino Acids (1987), John Wiley, New York, NY
6. Reviews:
7. Sardina F.J., and Rapoport H. Chem. Rev. 96 (1996) 1825-1872
8. Nájera C., and Yus M. Tetrahedron: Asymmetry 10 (1999) 2245-2303
9. Recent examples:
10. Flemer S., Wurthmann A., Mamai A., and Madalengoitia J.S. J. Org. Chem. 73 (2008) 7593-7602
11. Einsiedel J., Lanig H., Waibel R., and Gmeiner P. J. Org. Chem. 72 (2007) 9102-9113
12. Spiess S., Berthold C., Weihofen R., and Helmchen G. Org. Biomol. Chem. 5 (2007) 2357-2360
13. Alvarez de Cienfuegos L., and Langlois N. Tetrahedron: Asymmetry 17 (2006) 1863-1866
14. Milne C., Powell A., Jim J., Al Nakeeb M., Smith C.P., and Micklefield J. J. Am. Chem. Soc. 128 (2006) 11250-11259
15. Hanessian S., Gauchet C., Charron G., Marin J., and Nakache P. J. Org. Chem. 71 (2006) 2760-2778
16. Wipf P., Xu W., Kim H., and Takahashi H. Tetrahedron 53 (1997) 16575-16596
17. Oba M., Nishiyama N., and Nishiyama K. Chem. Commun. (2003) 776-777
18. Oba M., Nishiyama N., and Nishiyama K. Tetrahedron 61 (2005) 8456-8464
19. Corey E.J., and Raju N. Tetrahedron Lett. 24 (1983) 5571-5574
20. Blaskovich M.A., and Lajoie G.A. J. Am. Chem. Soc. 115 (1993) 5021-5030
21. Rose N.G.W., Blaskovich M.A., Evindar G., Wilkinson S., Luo Y., Fishlock D., Reid C., and Lajoie G.A. Org. Synth. 79 (2003) 216-227
22. Hansen D.B., Wan X., Carroll P.J., and Joullié M.M. J. Org. Chem. 70 (2005) 3120-3126
23. Hansen D.B., Lewis A.S., Gavalas S.J., and Joullie M.M. Tetrahedron: Asymmetry 17 (2006) 15-21
24. Herdeis C., and Kelm B. Tetrahedron 59 (2003) 217-229
25. Hara S., Makino K., and Hamada Y. Tetrahedron 60 (2004) 8031-8035
26. Soloshonok V.A., Ueki H., Tiwari R., Cai C., and Hruby V.J. J. Org. Chem. 69 (2004) 4984-4990
27. Jane D.E., Chalmers D.J., Howard J.A.K., Kilpatrick I.C., Sunter D.C., Thompson G.A., Udvarhelyi P.M., Wilson C., and Watkins J.C. J. Med. Chem. 39 (1996) 4738-4743
28. Davies J., Francis A.A., Oakes D.J., Sheardown M.J., and Watkins J.C. Neuropharmacology 24 (1985) 177-180
29. Zeise M.L., Knöpfel T., and Zieglgänsberger W. Brain Res. 443 (1988) 373-376
30. Collado I., Ezquerra J., Mateo A.I., and Rubio A. J. Org. Chem. 63 (1998) 1995-2001
31. Pedregal C., Ezquerra J., Escribano A., Carreño M.C., and García Ruano J.L. Tetrahedron Lett. 35 (1994) 2053-2056
32. Tsai C., Schnider J.A., and Lehmann J. Neurosci. Lett. 92 (1988) 298-302
33. Mann A., Boulanger T., Brandau B., Durant F., Evrard G., Haeulme M., Desaulles E., and Wermuth C.G. J. Med. Chem. 4 (1991) 1307-1313
34. Olpe H.P., Demikeville H., Baltzer W.L., Koella W.P., Wolf P., and Haas H.L. Eur. J. Pharmacol. 52 (1978) 133-136
35. Deng J., Duan Z.-C., Huang J.-D., Hu X.-P., Wang D.-Y., Yu S.-B., Xu X.-F., and Zheng Z. Org. Lett. 9 (2007) 4825-4828
36. Nemoto T., Jin L., Nakamura H., and Hamada Y. Tetrahedron Lett. 47 (2006) 6577-6581
37. Armstrong A., Convine N.J., and Popkin M.E. Synlett (2006) 1589-1591
38. Paraskar A.S., and Sudalai A. Tetrahedron 62 (2006) 4907-4916
39. Okino T., Hoashi Y., Furukawa T., Xu X., and Takemoto Y. J. Am. Chem. Soc. 127 (2005) 119-125
40. Becht J.-M., Meyer O., and Helmchen G. Synthesis 18 (2003) 2805-2810
41. Corey E.J., and Zhang F.-Y. Org. Lett. 2 (2000) 4257-4259
42. Chang M.-Y., Sun P.-P., Chen S.-T., and Chang N.-C. Tetrahedron Lett. 44 (2003) 5271-5273
43. Chang M.-Y., Chen C.-Y., Tasi M.-R., Tseng T.-W., and Chang N.-C. Synthesis (2004) 840-846
44. Xian M., Alaux S., Sagot E., and Gefflaut T. J. Org. Chem. 72 (2007) 7560-7566
45. Herdeis C., Hubmann H.P., and Lotter H. Tetrahedron: Asymmetry 5 (1994) 351-354
46. Karoyan P., and Chassaing G. Tetrahedron Lett. 43 (2002) 253-255