Chiral N β-Fmoc-amino alkyl isonitriles in Ugi-4CR: An assembly of novel 1,1′-iminodicarboxylated peptidomimetics

Tetrahedron

Volumn 68, Issue 7, 2012, Pages 1992-2000

  Narendra, N ^a   Vishwanatha, T M ^a   Nagendra, G ^a   Sureshbabu, Vommina V ^a  

^a BANGALORE UNIVERSITY   (India)

Author keywords

1,1 Iminodicarboxylic acid tethered peptidomimetics; Amino acid esters; N Fmoc amino alkyl isonitriles; Trifluoroacetic acid; U 4CR; U 5C 4CR

Indexed keywords

AMINO ACID; ESTER; ISONITRILE DERIVATIVE; PEPTIDOMIMETIC AGENT; SOLVENT; TRIFLUOROACETIC ACID;

ACIDITY; ARTICLE; CARBOXYLATION; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; PRIORITY JOURNAL; SOLVOLYSIS; SYNTHESIS; UGI FOUR COMPONENT REACTION;

EID: 84856365553     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.12.037     Document Type: Article

References (69)

1. S. Maeda, S. Komagawa, M. Uchiyama, and K. Morokuma Angew. Chem., Int. Ed. 49 2010 1
2. M. Passerini, and L. Simone Gazz. Chim. Ital. 51 1921 126
3. D. Enders, M.R.M. Huttl, C. Grondal, and G. Raabe Nature 441 2006 861
4. S. Marcaccini, and T. Torroba Nature 2 2007 632
5. J. Zhu, and H. Bienayme Multicomponent Reactions 2005 John Wiley & Sons Weinheim
6. A. Domling, and I. Ugi Angew. Chem., Int. Ed. 112 2002 3300
7. A. Domling Chem. Rev. 106 2006 17
8. T.A. Keating, and R.W. Armstrong J. Am. Chem. Soc. 118 1996 2574
9. S.L. Sollis J. Org. Chem. 70 2005 4735
10. I. Ugi Isonitrile Chemistry 1971 Academic New York, NY and London
11. J. Zhu, X. Wu, and S.J. Danishefsky Tetrahedron Lett. 50 2009 577
12. M. Mroczkiewicz, K. Winkler, D. Nowis, G. Placha, J. Golab, and R. Ostaszewski J. Med. Chem. 53 2010 1509
13. H.P. Hemantha, and V.V. Sureshbabu J. Pept. Sci. 16 2010 644
14. A.V. Gulevich, A.G. Zhdanko, R.V.A. Orru, and V.G. Nenajdenko Chem. Rev. 110 2010 5235
15. A.G. Zhdanko, and V.G. Nenajdenko J. Org. Chem. 74 2009 884
16. A.V. Gulevich, I.V. Shpilevaya, and V.G. Nenajdenko Eur. J. Org. Chem. 2009 3801
17. A.G. Zhdanko, A.V. Gulevich, and V.G. Nenajdenko Tetrahedron 65 2009 4692
18. A.V. Gulevich, N.E. Shevchenko, E.S. Balenkova, G.-V. Roschenthaler, and V.G. Nenajdenko Tetrahedron 64 2008 11706
19. X. Li, and S.J. Danishefsky J. Am. Chem. Soc. 130 2008 5446
20. G.O. Jones, X. Li, A.E. Hayden, K.N. Houk, and S.J. Danishefsky Org. Lett. 10 2008 4093
21. X. Li, Y. Yuan, W.F. Berkowitz, L.J. Todaro, and S.J. Danishefsky J. Am. Chem. Soc. 130 2008 13222
22. X. Li, Y. Yuan, C. Kan, and S.J. Danishefsky J. Am. Chem. Soc. 130 2008 13225
23. X. Wu, X. Li, and S.J. Danishefsky Tetrahedron Lett. 50 2009 1523
24. Y. Yuan, J. Zhu, X. Li, X. Wu, and S.J. Danishefsky Tetrahedron Lett. 50 2009 2329
25. X. Wu, Y. Yuan, X. Li, and S.J. Danishefsky Tetrahedron Lett. 50 2009 4666
26. X. Wu, J. Stockdill, P. Wang, and S.J. Danishefsky J. Am. Chem. Soc. 132 2010 4098
27. R. Bossio, S. Marcaccini, P. Paoli, and R. Pepino Synthesis 1994 672
28. M. Waki, and J. Meienhofer J. Am. Chem. Soc. 99 1977 6075
29. T. Yamada, Y. Omote, Y. Yamanaka, T. Miyazawa, and S. Kuwata Synthesis 1998 991
30. S. Faure, T. Hjelmgaard, S.P. Roche, and D.J. Aitken Org. Lett. 11 2009 11670
31. O.E. Vercillo, K.Z. Andrade, and L.A. Wessjohann Org. Lett. 10 2008 205
32. T. Tanino, S. Ichikawa, M. Shiro, and A. Matsuda J. Org. Chem. 75 2010 1366
33. J. Zhu Eur. J. Org. Chem. 2003 1133
34. J.-M. Grassot, G. Masson, and J. Zhu Angew. Chem., Int. Ed. 47 2008 947
35. J.E. Biggs-Houck, A. Younai, and J.T. Shaw Curr. Opin. Chem. Biol. 14 2010 371
36. A. Ulaczyak-Lesanko, and D.G. Hall Curr. Opin. Chem. Biol. 9 2005 266
37. S.M. Bauer, and R.W. Armstrong J. Am. Chem. Soc. 121 1999 6355
38. H.P. Isenring, and W. Hofheinz Tetrahedron 39 1983 2591
39. A. Domling, and I. Ugi Angew. Chem., Int. Ed. Engl. 32 1993 563
40. P.-C. Huang, G.-J. Hsu, B.-R. Zhuang, and K. Sung Amino Acids 34 2008 449
41. W.H. Wang, X.M. Zou, X. Zhang, Y.Q. Fu, and P. Xu Chin. Chem. Lett. 16 2005 585
42. A. Domling, K.-Z. Chi, and M. Barrere Bioorg. Med. Chem. Lett. 9 1999 2871
43. A. Domling Nucleotides Nucleosides 17 1998 1667
44. V.V. Sureshbabu, N. Narendra, and G. Nagendra J. Org. Chem. 74 2009 153
45. G. Chennakrishnareddy, G., Nagendra, H.P. Hemantha, U. Das, T.N. Guru Row, and V.V. Sureshbabu Tetrahedron 66 2010 6178
46. N.S. Sudarshan, N. Narendra, H.P. Hemantha, and V.V. Sureshbabu J. Org. Chem. 72 2007 9804
47. B.S. Patil, G.-R. Vasanthkumar, and V.V. Sureshbabu J. Org. Chem. 68 2003 7274
48. S.J. Park, G. Keum, S.B. Kang, H.Y. Koh, Y. Kim, and D.H. Lee Tetrahedron Lett. 39 1998 7109
49. H.P. Isenring, and W. Hofheinz Synthesis 1981 385
50. S. Gedey, J. Van der Eycken, and F. Fulop Org. Lett. 4 2002 1967
51. H. Nitta, M. Hatanaka, and T. Ishimaru J. Chem. Soc., Chem. Commun. 1987 51
52. A. Domling, B. Beck, U. Eichelberger, S. Sakamuri, S. Menon, Q.-Z. Chen, Y. Lu, and L.A. Wessjohann Angew. Chem., Int. Ed. 45 2006 7235
53. P. Tempest, V. Gore, and C. Hulme Tetrahedron Lett. 44 2003 1947
54. S.P. Raillard, G. Ji, A.D. Mann, and T.A. Baer Org. Process Res. Dev. 3 1999 177
55. C. Faggi, S. Marcaggini, R. Pepino, and M.C. Pozo Synthesis 2002 2756 2760
56. S. Berłozecki, W. Szymanski, and R. Ostaszewski Tetrahedron 64 2008 9780
57. A. Demharter, W. Horl, E. Herdtweck, and I. Ugi Angew. Chem., Int. Ed. 35 1996 173
58. I. Ugi, A. Demharter, W. Horl, and T. Schmid Tetrahedron 52 1996 11657
59. M. Bachman, S.E. Mann, and T.D. Sheppard Org. Biomol. Chem. 10 2012 162 170
60. K. Sung, F.-L. Chen, and M.-J. Chung Mol. Divers. 6 2003 213
61. G. Dyker, k. Breitenstein, and G. Henkel Tetrahedron: Asymmetry 13 2002 1929
62. S. Fushiya, S. Yamada, M. Matsuda, and S. Nozoe Tetrahedron Lett. 35 1994 8201
63. J. Tempe B. Weinstein, Chemistry and Biochemistry of Amino Acids, Peptides and Proteins 7 1993 Marcel Dekker New York, NY 1134
64. K. Ananda, and V.V. Sureshbabu J. Pept. Res. 57 2001 223
65. H. Ding, and G.K. Friestad Org. Lett. 6 2004 637
66. R.J. Bergeron, and J.J. McManis J. Org. Chem. 53 1988 3108
67. H. Newmann J. Org. Chem. 30 1979 1287
68. M. Imazawa, and F. Eckstein J. Org. Chem. 44 1979 2039
69. C. Spencer, J. Balsells, and H. Li Tetrahedron Lett. 50 2009 1010