An overview on the synthesis of furanoid and pyranoid sugar α- And β-amino acids and related aminocycloalkanecarboxylic acids from carbohydrates

Comptes Rendus Chimie

Volumn 14, Issue 2-3, 2011, Pages 313-326

  Soengas, Raquel G ^a   Estévez, Amalia M ^a   Estévez, Juan C ^a   Estévez, Ramón J ^a  

^a Universidade de Santiago de Compostela ^*  (Spain)

Author keywords

Amino acids; Asymmetric synthesis; Carbocycles; Carbohydrates; Chiral pool; Heterocycles

Indexed keywords

EID: 79951954037     PISSN: 16310748     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.crci.2010.11.003     Document Type: Short Survey

References (115)

1. K.C. Nicolaou, D. Vourloumis, N. Winssinger, and P.S. Baran Angew. Chem., Int. Ed. 39 2000 44
2. D.L. Levy, P. Fügedi (Eds.), The Organic Chemistry of Sugars, Taylor & Francis Group, 2006.
3. F. Schweizer, and O. Hindsgaul Curr. Opin. Chem. Biol. 3 1999 291
4. P.H. Seeberger, and W.C. Haase Chem. Rev. 100 2000 4349
5. P. Sears, and C.H. Wong Science 291 2001 2344
6. K. Larsen, M.B. Thygesen, F. Guillaumie, W.G.T. Willats, and K.J. Jensen Carbohydr. Res. 341 2006 1209
7. P.H. Seeberger, and D.B. Werz Nature 446 2007 1046
8. P.H. Seeberger Carbohydr. Res. 343 2008 1889
9. Y. Chapleur, Carbohydrate Mimics 1998 Wiley-VCH New York p. 87
10. S.A.W. Gruner, E. Locardi, E. Lohof, and H. Kessler Chem. Rev. 102 2002 491
11. T.K. Chakraborty, P. Srinivasu, S. Tapadar, and B.K. Mohan J. Chem. Sci. 116 2004 187
12. O. Arjona, A.M. Gómez, J.C. López, and J. Plumet Chem. Rev. 107 2007 1919
13. D. Seebach, M. Brenner, M. Rueping, B. Schweizer, and B. Jaun Chem. Commun. 2001 207
14. S. Hanessian, X. Luo, R. Schaum, and S. Michnick J. Am. Chem. Soc. 120 1998 8569
15. D. Seebach, M. Brener, M. Rueping, and B. Jaun Chem. Eur. J. 8 2002 573
16. S. Hanessian, X. Luo, and R. Schaum Tetrahedron Lett. 40 1999 4925
17. M. Brener, and D. Seebach Helv. Chim. Acta 84 2001 2155
18. A. Dondoni, and A. Marra Chem. Rev. 100 2000 4395
19. T.K. Chakraborty, S. Ghosh, and S. Jayaprakash Curr. Med. Chem. 9 2002 421
20. F. Schweizer Angew. Chem. Int. Ed. 41 2002 230
21. T.K. Chakraborty, P. Srinivasu, S. Tapadar, and B.K. Mohan Glycoconj. J. 22 2005 83
22. C. Cativela, and M.D. Díaz de Villegas Tetrahedron: Asymm. 11 2000 645
23. F. Clerici, M.L. Gelmi, A. Gambini, and D. Nava Tetrahedron 57 2001 6429
24. S.H. Gellman Acc. Chem. Res. 31 1998 173
25. T. Yamazaki, A. Probsti, P.W. Schiller, and M. Goodman Int. J. Pept. Protein Res. 37 1991 364
26. M.D.P. Risseeuw, M. Overhand, G.W.J. Fleet, and M.I. Simone Tetrahedron: Asymm. 18 2007 2001
27. Y.D. Wu, and S. Gellman Acc. Chem. Res. 41 2008 1231
28. S. Omura, M. Murata, N. Imamura, Y. Iwai, H. Tanaka, A. Furusali, and T. Matsumoto J. Antibiot. 37 1984 1324
29. S.F. Barker, D. Angus, C. Tailleufumier, M.R. Probert, D.J. Watkin, M.P. Watterson, T.D.W. Claridge, N.L. Hugenford, and G.W.J. Fleet Tetrahedron Lett. 42 2001 4247
30. T.D.W. Claridge, J.M. Goodman, A. Moreno, D. Angus, S.F. Barker, C. Tailleufumier, M.P. Watterson, and G.W.J. Fleet Tetrahedron Lett. 42 2001 4251
31. J.J. Fox, Y. Kuwada, and K.A. Watanabe Tetrahedron Lett. 2 1968 6029
32. K. Isono, K. Asahi, and S. Suzuki J. Am. Chem. Soc. 91 1969 7490
33. F.W. Lichtenthaler, T. Morino, and H.M. Menzel Tetrahedron Lett. 9 1975 665
34. J.P. Waltho, D.H. Williams, E. Selva, and P. Ferrari J. Chem. Soc., Perkin Trans. I 9 1987 2103
35. K. Heyns, and H. Paulsen Chem. Ber. 88 1955 188
36. H. Kessler, B. Diefenbach, D. Finsinger, A. Geyer, M. Gurrath, S.L. Goodman, G. Hoelzemann, R. Haubner, and A. Jonczyk Lett. Pept. Sci. 2 1995 155
37. E. Graf von Roedern, E. Lohof, G. Hessler, M. Hoffman, and H. Kessler J. Am. Chem. Soc. 118 1996 10156
38. T.K. Chakraborty, S. Jayaprakash, and S. Ghosh Comb. Chem. 5 2002 373
39. M. Nakajima, K. Itoi, Y. Takamatsu, T. Kinoshita, T. Okazaki, K. Kawakubo, M. Shindo, T. Honma, M. Tohjigamori, and T. Haneishi J. Antibiot. 44 1991 293
40. AG. Ciba-Geigi, DE Pat. 4,129,616 A1, 1990.
41. MitsubishiKasei Corp. Jpn. Pat. 04/222,589 A, 1990.
42. A. Renard, M. Kotera, and J. Lhomme Tetrahedron Lett. 39 1998 3129
43. A. Renard, M. Kotera, M.C. Brochier, and J. Lhomme Eur. J. Org. Chem. 2000 1831
44. H. Sano, and S. Sugai Tetrahedron 51 1995 4635
45. J.W. Burton, J.C. Son, A.J. Fairbanks, S.S. Choi, H. Taylor, D.J. Watkin, B.G. Winchester, and G.W.J. Fleet Tetrahedron Lett. 34 1993 6119
46. C.J.F. Bichard, E.P. Mitchell, M.R. Wormald, K.A. Watson, L.N. Johnson, S.E. Zographos, D.D. Koutra, N.G. Oikonomakos, and G.W.J. Fleet Tetrahedron Lett. 36 1995 2145
47. J.C. Estevez, M.D. Smith, M.R. Wormald, G.S. Besra, P.J. Brennan, R.J. Nash, and G.W.J. Fleet Tetrahedron: Asymm. 7 1996 391
48. E. Osz, E. Sos, L. Somsak, L. Szilagyi, and Z. Dinya Tetrahedron 53 1997 5813
49. J.C. Estevez, M.D. Smith, A.L. Lane, S. Crook, D.J. Watkins, G.S. Besra, P.J. Brennan, R.J. Nash, and G.W.J. Fleet Tetrahedron: Asymm. 7 1996 387
50. Y.S. Agasimundin, M.W. Mumper, and R.S. Hosmane Bioorg. Med. Chem. 6 1998 911
51. T.M. Krulle, K.A. Watson, M. Gregoriou, L.N. Johnson, S. Crook, D.J. Watkin, R.C. Griffiths, R.J. Nash, K.E. Tsitsanou, S.E. Zographos, N.G. Oikonomakos, and G.W.J. Fleet Tetrahedron Lett. 36 1995 8291
52. J.C. Estevez, J.W. Burton, R.J. Estevez, H. Ardron, M.R. Wormald, R.A. Dwek, D. Brown, and G.W.J. Fleet Tetrahedron: Asymm. 9 1998 2137
53. R.G. Soengas, J.C. Estevez, and R.J. Estevez Tetrahedron: Asymm. 14 2003 3955
54. J.C. Estevez, J. Saunders, G.S. Besra, P.J. Brennan, R.J. Nash, and G.W.J. Fleet Tetrahedron: Asymm. 7 1996 383
55. M. Lakhrissi, and Y. Chapleur J. Org. Chem. 59 1994 5752
56. M. Lakhrissi, and Y. Chapleur Tetrahedron Lett. 39 1998 4659
57. A. Dondoni, and M.C. Scherrmann J. Org. Chem. 59 1994 6404
58. A. Dondoni, M.C. Scherrmann, A. Marra, and J.L. Delepine J. Org. Chem. 59 1994 7517
59. D.L. Long, R.J. Tennant-Eyles, J.C. Estévez, M.R. Wormald, R.A. Dwek, M.D. Smith, and G.W.J. Fleet J. Chem. Soc., Perkin Trans. I 2001 807
60. A. Dondoni, and M.C. Scherrmann Tetrahedron Lett. 34 1993 7319
61. D.J. MacNeil, and M.A. Bednarek Peptides 30 2009 2008
62. M. Porcelloni, P. D'Andrea, M. Altamura, R.M. Catalioto, S. Giuliani, S. Meini, and D. Fattori Bioorg. Med. Chem. Lett. 18 2008 4705
63. E. Sikorska, and S. Rodziewicz-Motowidlo J. Pept. Sci. 14 2008 819
64. A.J. Fairbanks, A. Hui, B.M. Skead, P.M. de, Q. Lilley, R.B. Lamont, R. Storer, J. Sauders, D.J. Watkin, and G.W.J. Fleet Tetrahedron Lett. 35 1994 8891
65. A. Hui, A.J. Fairbanks, R.J. Nash, P.M. de, Q. Lilley, R. Storer, D.J. Watkin, and G.W.J. Fleet Tetrahedron Lett. 35 1994 8895
66. A.J. Fairbanks, R.P. Elliott, C. Smith, A. Hui, G. Way, R. Storer, H. Taylor, D.J. Watkin, B.G. Winchester, and G.W.J. Fleet Tetrahedron Lett. 34 1993 7953
67. R.G. Soengas, J.C. Estévez, R.J. Estévez, and M.A. Maestro Tetrahedron: Asymm. 14 2003 1653
68. A.F. Abdel-Magid, and J.H. Cohen C. A Maryanoff. Curr. Med. Chem. 6 1999 955
69. E. Juaristi, and H. Lopez-Ruiz Curr. Med. Chem. 6 1999 983
70. F. Fülöp Chem. Rev. 101 2001 2181
71. K.H. Park, and M.J. Kurth Tetrahedron 58 2002 8629
72. J.A. Miller, and S.T. Nguyen Mini-Rev. Org. Chem. 2 2005 39
73. E.G. von Roedern, and H. Kessler Angew. Chem. Int. Ed. Engl. 33 1994 687
74. S.A.W. Gruner, G. Kéri, R. Schwab, A. Venetianer, and H. Kessler Org. Lett. 3 2001 3723
75. S.A.W. Gruner, V. Truffault, G. Voll, E. Locardi, M. Stôckle, and H. Kessler Chem. Eur. J. 8 2002 4365
76. J.P. McDevitt, and T.P. Lansbury J. Am. Chem. Soc. 118 1996 3818
77. M.P. DeNinno, H. Masamune, L.K. Chenard, K.J. DiRico, C. Eller, J.B. Etienne, J.E. Tickner, S.P. Kennedy, D.R. Knight, J. Kong, J.J. Oleynek, W.R. Tracey, and R.J. Hill J. Med. Chem. 46 2003 353
78. M.P. Watterson, L. Pickering, M.D. Smith, S.J. Hudson, P.R. Marsh, J.E. Mordaunt, D.J. Watkin, C.J. Newman, and G.W.J. Fleet Tetrahedron: Asymm. 10 1999 1855
79. A.A. Edwards, G.J. Sanjayan, J. Gangadharar, S. Hachisu, R. Soengas, A. Stewart, G.E. Tranter, and G.W.J. Fleet Tetrahedron 62 2006 4110
80. R.A. Dwek, T.D. Butters, F.M. Platt, and N. Zitzmann Nat. Rev. Drug Discov. 1 2002 65
81. M. Hoffman, F. Burkhart, G. Hessler, and H. Kessler Helv. Chim. Acta 79 1996 1519
82. C.D. Warren, and R.W. Jeanloz Carb. Res. 53 1977 67
83. C.D. Warren, M.A.E. Shaban, and R.W. Jeanloz Carb. Res. 59 1977 427
84. Y. Suhara, J.E.K. Hildreth, and Y. Ichikawa Tetrahedron Lett. 37 1996 1575
85. R.W. Myers, and Y.C. Lee Carb. Res. 132 1984 61
86. C. Vogel, and P. Gries J. Carb. Chem. 13 1994 37
87. D. Mostowicz, and M. Chmielewski Carb. Res. 257 1994 137
88. M. Konishi, M. Nishio, K. Saitoh, T. Miyaki, T. Oki, and H. Kawaguchi J. Antibiotics 42 1989 1749
89. T. Iwamoto, E. Tsujii, M. Ezaki, A. Fujie, S. Hashimoto, M. Okuhara, M. Kohsaka, H. Imanaka, and K. Kawabata J. Antibiotics 43 1990 1
90. J. Mittendorf, F. Kunisch, M. Matzke, H.C. Militzer, A. Schmidt, and W. Schönfeld Bioorg. Med. Chem. Lett. 13 2003 433
91. Z. Hamersak, M. Roje, A. Avdagic, and V. Sunjic Tetrahedron: Asymm. 18 2007 635
92. D.J. Hill, M.J. Mio, R.B. Prince, T.S. Hughes, and J.S. Moore Chem. Rev. 101 2001 3893
93. D. Yang, D.W. Zhang, Y. Hao, Y.D. Wu, S.W. Luo, and N.Y. Zhu Angew. Chem., Int. Ed. 43 2004 6719
94. N. Rathore, S.H. Gellman, and J.J. de Pablo Biophys. J. 91 2006 3425
95. G.R. Cook, and J.R. Stille Tetrahedron Lett. 35 1994 1669
96. S.K. Kang, and D.H. Lee Synlett 1991 175
97. K. Hattori, and H. Yamamoto Tetrahedron 50 1994 2785
98. D.G. Melillo, R.J. Cvetovich, K.M. Ryan, and M. Sletzinger J. Org. Chem. 51 1986 1498
99. R.P. Cheng, S.H. Gellman, and W.F. DeGrado Chem. Rev. 101 2001 3219
100. O. Roy, S. Faure, and D.J. Aitken Tetrahedron Lett. 47 2006 5981
101. S. Chandrasekhar, A. Sudhakar, M.U. Kiran, B.N. Babu, and B. Jagadeesh Tetrahedron Lett. 49 2008 7368
102. F. Rua, S. Boussert, T. Parella, I. Diez-Perez, V. Branchadell, E. Giralt, and R.M. Ortuno Org. Lett. 9 2007 3643
103. V. D'Elia, H. Zwicknagl, and O. Reiser J. Org. Chem. 73 2008 3262
104. A. Hetényi, Z. Szakonyi, I.M. Mándity, É. Szolnoki, G.K. Tóth, T.A. Martinek, and F. Fülöp Chem. Commun. 2009 177
105. F. Fülöp, T.A. Martinek, and G.K. Tóth Chem. Soc. Rev. 35 2006 323
106. T.A. Martinek, G.K. Tóth, E. Vass, M. Hollósi, and F. Fülöp Angew. Chem., Int. Ed. 41 2002 1718
107. I.M. Mándity, E. Wéber, T.A. Martinek, G. Olajos, G.K. Tóth, E. Vass, and F. Fülöp Angew. Chem., Int. Ed. 48 2009 2171
108. M. Palkó, L. Kis, and F. Fülöp Curr. Med. Chem. 12 2005 3063
109. R.M. Ortuño, A.G. Moglioni, and G.Y. Moltrasio Curr. Org. Chem. 9 2005 237
110. S.G. Davies, A.D. Smith, and P.D. Price Tetrahedron: Asymm. 16 2005 2833
111. R.P. Elliott, A. Hui, A.J. Fairbanks, R.J. Nash, B.G. Winchester, G. Way, C. Smith, R.B. Lamont, R. Storer, and G.W.J. Fleet Tetrahedron Lett. 34 1993 7949
112. R.G. Soengas, B. Pampín, J.C. Estevez, and R.J. Estevez Tetrahedron: Asymm. 16 2005 205
113. R.G. Soengas, J.C. Estevez, and R.J. Estevez Org. Lett. 5 2003 1423
114. F. Fernandez, F. Sussman, J.C. Estevez, and R.J. Estevez Tetrahedron: Asymm. 19 2008 2907
115. F. Fernández, A.M. Estevez, J.C. Estevez, and R.J. Estevez Tetrahedron: Asymm. 20 2009 892