Formation of septanoses from hexopyranosides via 5,6-exo-glycals

Carbohydrate Research

Volumn 356, Issue , 2012, Pages 93-103

  Jackowski, Olivier ^a   Chrétien, Françoise ^a   Didierjean, Claude ^b   Chapleur, Yves ^a  

^a NANCY UNIVERSITÉ   (France)

^b Nancy University CNRS   (France)

Author keywords

1,6 Anhydro bridge opening; Dihydroxylation; exo Glycal; Radical deoxygenation; Septanose

Indexed keywords

1,6-ANHYDRO BRIDGE OPENING; DEOXYGENATIONS; DIHYDROXYLATION; EXO-GLYCAL; SEPTANOSE;

ORGANIC COMPOUNDS; SYNTHESIS (CHEMICAL);

HYDROXYLATION;

5,6 EXO GLYCAL; GLUCONATE CALCIUM; HEPTOSE; METHYL DEXTRO HEXO 5 ULOSIDE; PYRANOSIDE; UNCLASSIFIED DRUG;

ANHYDROBIOSIS; CONFERENCE PAPER; CONFORMATION; DIHYDROXYLATION; PRIORITY JOURNAL;

CATALYSIS; GLUCOSE; GLYCOSIDES; MESYLATES; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; OXYGEN;

EID: 84862307083     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2012.02.026     Document Type: Conference Paper

References (98)

1. J.D. Stevens J. Chem. Soc. D. 1969 1140 1141
2. J.D. Stevens, J.P. Beale, and N.C. Stephenson J. Chem. Soc. D. 1971 484 486
3. J.F. McConnell, and J.D. Stevens J. Chem. Soc., Perkin Trans. 2 1974 354 358
4. W. Choong, J.F. McConnell, N.C. Stephenson, and J.D. Stevens Aust. J. Chem. 33 1980 979 985
5. V.J. James, and J.D. Stevens Carbohydr. Res. 82 1980 167 174
6. C.J. Ng, and J.D. Stevens Carbohydr. Res. 284 1996 241 248
7. G.E. Driver, and J.D. Stevens Carbohydr. Res. 334 2001 81 89
8. T.Q. Tran, and J.D. Stevens Aust. J. Chem. 55 2002 171 178
9. J. Jackobs, M.A. Reno, and M. Sundaralingam Carbohyd. Res. 28 1973 75 85
10. M.-O. Contour, C. Fayet, and J. Gelas Carbohydr. Res. 201 1990 150 152
11. C. Pavlik, A. Onorato, S. Castro, M. Morton, M. Peczuh, and M.B. Smith Org. Lett. 11 2009 3722 3725
12. M. Sasaki, and H. Fuwa Nat. Prod. Rep. 25 2008 401 426
13. K.C. Nicolaou, M.O. Frederick, and R.J. Aversa Angew. Chem., Int. Ed. 47 2008 7182 7225
14. J.O. Hoberg Tetrahedron 54 1998 12631 12670
15. J.S. Clark Chem. Commun. 2006 3571 3581
16. N.L. Snyder, H.M. Haines, and M.W. Peczuh Tetrahedron 62 2006 9301 9320
17. Y. Chapleur Carbohydrate Mimics 1998 Weinheim Wiley-VCH pp 1-604
18. S. Castro, M. Duff, N.L. Snyder, M. Morton, C.V. Kumar, and M.W. Peczuh Org. Biomol. Chem. 3 2005 3869 3872
19. A. Tauss, A.J. Steiner, A.E. Stuetz, C.A. Tarling, S.G. Withers, and T.M. Wrodnigg Tetrahedron: Asymmetry 17 2006 234 239
20. S. Castro, W.S. Fyvie, S.A. Hatcher, and M.W. Peczuh Org. Lett. 7 2005 4709 4712
21. D. Sabatino, and M.J. Damha Nucleosides Nucleotides Nucleic Acids 26 2007 1185 1188
22. D. Sabatino, and M.J. Damha J. Am. Chem. Soc. 129 2007 8259 8270
23. G. Sizun, J.-F. Griffon, L. Griffe, D. Dukhan, R. Storer, J.-P. Sommadossi, A.G. Loi, C. Musiu, B. Poddesu, A. Cadeddu, M. Fanti, N. Boscu, F. Bassetti, M. Liuzzi, and G. Gosselin Nucleic Acids Symp. Ser. 52 2008 611 612
24. M.A. Boone, F.E. McDonald, J. Lichter, S. Lutz, R. Cao, and K.I. Hardcastle Org. Lett. 11 2009 851 854
25. J.O. Hoberg J. Org. Chem. 62 1997 6615 6618
26. J.O. Hoberg, and J.J. Bozell Tetrahedron Lett. 36 1995 6831 6834
27. J.O. Hoberg, and D.J. Claffey Tetrahedron Lett. 37 1996 2533 2536
28. R. Batchelor, and J.O. Hoberg Tetrahedron Lett. 44 2003 9043 9045
29. R. Batchelor, J.E. Harvey, P.T. Northcote, P. Teesdale-Spittle, and J.O. Hoberg J. Org. Chem. 74 2009 7627 7632
30. N.V. Ganesh, and N. Jayaraman J. Org. Chem. 72 2007 5500 5504
31. N.V. Ganesh, and N. Jayaraman J. Org. Chem. 74 2009 739 746
32. Y. Sugita, C. Kimura, and I. Yokoe Heterocycles 55 2001 855 859
33. Y. Sugita, C. Kimura, H. Hosoya, S. Yamadoi, and I. Yokoe Tetrahedron Lett. 42 2001 1095 1098
34. J. Saha, and M.W. Peczuh Org. Lett. 11 2009 4482 4484
35. G.S. Cousins, and J.O. Hoberg Chem. Soc. Rev. 29 2000 165 174
36. N.V. Ganesh, S. Raghothama, R. Sonti, and N. Jayaraman J. Org. Chem. 75 2010 215 218
37. R.J. Hewitt, and J.E. Harvey J. Org. Chem. 75 2010 955 958
38. S. Castro, C.S. Johnson, B. Surana, and M.W. Peczuh Tetrahedron 65 2009 7921 7926
39. M.W. Peczuh, and N.L. Snyder Tetrahedron Lett. 44 2003 4057 4061
40. M.W. Peczuh, N.L. Snyder, and W.S. Fyvie Carbohydr. Res. 339 2004 1163 1171
41. W.S. Fyvie, M. Morton, and M.W. Peczuh Carbohydr. Res. 339 2004 2363 2370
42. M.P. DeMatteo, N.L. Snyder, M. Morton, D.M. Baldisseri, C.M. Hadad, and M.W. Peczuh J. Org. Chem. 70 2005 24 38
43. M.P. DeMatteo, S. Mei, R. Fenton, M. Morton, D.M. Baldisseri, C.M. Hadad, and M.W. Peczuh Carbohydr. Res. 341 2006 2927 2945
44. S. Castro, E.C. Cherney, N.L. Snyder, and M.W. Peczuh Carbohydr. Res. 342 2007 1366 1372
45. B. Schmidt, and A. Biernat Org. Lett. 10 2008 105 108
46. V.H. Jadhav, O.P. Bande, R.V. Pinjari, S.P. Gejji, V.G. Puranik, and D.D. Dhavale J. Org. Chem. 74 2009 6486 6494
47. J.C.Y. Wong, P. Lacombe, and C.F. Sturino Tetrahedron Lett. 40 1999 8751 8754
48. H. Ovaa, M.A. Leeuwenburgh, H.S. Overkleeft, G.A. van der Marel, and J.H. van Boom Tetrahedron Lett. 39 1998 3025 3028
49. W.S. Fyvie, and M.W. Peczuh J. Org. Chem. 73 2008 3626 3629
50. S.D. Markad, S. Xia, N.L. Snyder, B. Surana, M.D. Morton, C.M. Hadad, and M.W. Peczuh J. Org. Chem. 73 2008 6341 6354
51. E. Alcazar, J.M. Pletcher, and F.E. McDonald Org. Lett. 6 2004 3877 3880 and references cited therein
52. S. Castro, and M.W. Peczuh J. Org. Chem. 70 2005 3312 3315
53. C.J. Ng, D.C. Craig, and J.D. Stevens Carbohydr. Res. 284 1996 249 263
54. C.J. Bailey, D.C. Craig, C.T. Grainger, V.J. James, and J.D. Stevens Carbohydr. Res. 284 1996 265 270
55. C. Taillefumier, M. Lakhrissi, and Y. Chapleur Synlett 1999 697 700
56. P.M. Enright, M. Tosin, M. Nieuwenhuyzen, L. Cronin, and P.V. Murphy J. Org. Chem. 67 2002 3733 3741
57. F. Chrétien, M. Khaldi, and Y. Chapleur Synth. Commun. 20 1990 1589 1596
58. C.-C. Wang, S.-Y. Luo, C.-R. Shie, and S.-C. Hung Org. Lett. 4 2002 847 849
59. F. Chrétien Synth. Commun. 19 1989 1015 1024
60. W.M. Doane, B.S. Shasha, C.R. Russell, and C.E. Rist J. Org. Chem. 30 1965 3071 3075
61. E.I. Stout, W.M. Doane, B.S. Shasha, C.R. Russell, and C.E. Rist Carbohydr. Res. 3 1967 354 360
62. B.S. Shasha, W.M. Doane, C.R. Russell, and C.E. Rist Carbohydr. Res. 6 1968 34 42
63. B.S. Shasha, W.M. Doane, C.R. Russell, and C.E. Rist J. Org. Chem. 34 1969 1642 1645
64. D.H.R. Barton, P.I. Dalko, and S.D. Géro Tetrahedron Lett. 33 1992 1883 1886
65. E.A. Castro, M. Aliaga, M. Gazitúa, and J.G. Santos Tetrahedron 62 2006 4863 4869
66. E.A. Castro, M. Cubillos, and J.G. Santos J. Org. Chem. 69 2004 4802 4807
67. D.H.R. Barton, W. Hartwig, R.S.H. Motherwell, W.B. Motherwell, and A. Stange Tetrahedron Lett. 23 1982 2019 2022
68. S.C. Dolan, and J. MacMillan J. Chem. Soc., Chem. Commun. 1985 1588 1589
69. D.H.R. Barton, and D. Crich J. Chem. Soc., Chem. Commun. 1984 774 775
70. D.H.R. Barton, and D. Crich Tetrahedron Lett. 26 1985 757 760
71. D.H.R. Barton, and D. Crich J. Chem. Soc., Perkin Trans. 1 1986 1603 1611
72. D.O. Jang, D.H. Cho, and J. Kim Synth. Commun. 28 1998 3559 3565
73. D.H.R. Barton, S.I. Parekh, and C.L. Tse Tetrahedron Lett. 34 1993 2733 2736
74. J. Xu, and J.C. Yadan Tetrahedron Lett. 37 1996 2421 2424
75. A.P. Kozikowski, T.R. Nieduzak, T. Konoike, and J.P. Springer J. Am. Chem. Soc. 109 1987 5167 5175
76. K.C. Nicolaou, P. Maligres, T. Suzuki, S.V. Wendeborn, W.M. Dai, and R.K. Chadha J. Am. Chem. Soc. 114 1992 8890 8907
77. K.C. Nicolaou, and W.M. Dai J. Am. Chem. Soc. 114 1992 8908 8921
78. D.H.R. Barton, and S.W. McCombie J. Chem. Soc., Perkin Trans. 1 1975 1574 1585
79. D. Crich, A.L.J. Beckwith, C. Chen, Q. Yao, I.G.E. Davison, R.W. Longmore, C. Anaya de Parrodi, L. Quintero-Cortes, and J. Sandoval-Ramirez J. Am. Chem. Soc. 117 1995 8757 8768
80. F. Baumberger, and A. Vasella Helv. Chim. Acta 66 1983 2210 2222
81. J. Dupuis, B. Giese, D. Rüegge, H. Fischer, H.-G. Korth, and R. Sustmann Angew. Chem., Int. Ed. Engl. 23 1984 896 898
82. J.-P. Praly Adv. Carbohydr. Chem. Biochem. 56 2001 65 151
83. D. Rolf, J.A. Bennek, and G.R. Gray J. Carbohydr. Chem. 2 1983 373 383
84. M.D. Lewis, J.K. Cha, and Y. Kishi J. Am. Chem. Soc. 104 1982 4976 4978
85. M. Terauchi, H. Abe, A. Matsuda, and S. Shuto Org. Lett. 6 2004 3751 3754
86. M. Cerný Adv. Carbohydr. Chem. Biochem. 58 2003 121 198
87. J.-C. Lee, S.-W. Chang, C.-C. Liao, F.-C. Chi, C.-S. Chen, Y.-S. Wen, C.-C. Wang, S.S. Kulkarni, R. Puranik, Y.-H. Liu, and S.-C. Hung Chem. Eur. J. 10 2004 399 415
88. R.T. Dere, Y. Wang, and X. Zhu Org. Biomol. Chem. 6 2008 2061 2063
89. X. Zhu, R.T. Dere, J. Jiang, L. Zhang, and X. Wang J. Org. Chem. 76 2011 10187 10197
90. S. Arndt, and L.C. Hsieh-Wilson Org. Lett. 5 2003 4179 4182
91. M. Zottola, B.V. Rao, and B. Fraser-Reid J. Chem. Soc., Chem. Commun. 10 1991 969 970
92. C.S. Burgey, R. Vollerthun, and B. Fraser-Reid Tetrahedron Lett. 35 1994 2637 2640
93. J.-C. Lee, C.-A. Tai, and S.-C. Hung Tetrahedron Lett. 43 2002 851 855
94. R. Dumeunier, and I.E. Markó Tetrahedron Lett. 45 2004 825 829
95. A. Dzudza, and T.J. Marks J. Org. Chem. 73 2008 4004 4016
96. K. Sato, N. Kubo, R. Takada, and S. Sakuma Bull. Chem. Soc. Jpn. 66 1993 1156 1165
97. P. Deslongchamps, C. Moreau, D. Frehel, and R. Chenevert Can. J. Chem. 53 1975 1204 1211
98. P. Kovac Carbohyd. Res. 31 1973 323 330