Recent advances in the stereoselective synthesis of carbohydrate 2-C-analogs

Organic and Biomolecular Chemistry

Volumn 10, Issue 12, 2012, Pages 2351-2362

  Yin, Jian ^a,b   Linker, Torsten ^b  

^a JIANGNAN UNIVERSITY   (China)

^b UNIVERSITY OF POTSDAM   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL POLYSACCHARIDES; C-GLYCOSIDES; FUNCTIONALIZED; GLYCALS; GLYCOSYL; GOOD YIELD; MACROLIDES; RADICAL ADDITION; RING OPENING; STEREOSELECTIVE SYNTHESIS; SYNTHETIC CHEMISTS;

BROMINE COMPOUNDS; DRUG PRODUCTS; STEREOCHEMISTRY; STEREOSELECTIVITY; SUGARS;

ORGANIC COMPOUNDS;

AMINO ACID; CARBOHYDRATE; PLATINUM;

CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; OXIDATION REDUCTION REACTION; REVIEW; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; CARBOHYDRATES; CATALYSIS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PLATINUM; STEREOISOMERISM;

BACTERIA (MICROORGANISMS);

EID: 84858045433     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c2ob06529k     Document Type: Review

References (130)

1. D. B. Werz P. H. Seeberger Chem.-Eur. J. 2005 11 3194 3206
2. P. Stallforth B. Lepenies A. Adibekian P. H. Seeberger J. Med. Chem. 2009 52 5561 5577
3. T. J. Boltje T. Buskas G.-J. Boons Nat. Chem. 2009 1 611 622
4. P. H. Seeberger D. B. Werz Nature 2007 446 1046 1051
5. M. Markert R. Mahrwald Chem.-Eur. J. 2008 14 40 48
6. S. Muthana H. Cao X. Chen Curr. Opin. Chem. Biol. 2009 13 573 581
7. R. Mahajan N. K. Khare Trends Carbohydr. Res. 2010 2 28 53
8. D. C. Koester A. Holkenbrink D. B. Werz Synthesis 2010 19 3217 3242
9. I. Robina A. T. Carmona A. J. Moreno-Vargas E. Moreno-Clavijo Chimia 2011 65 85 90
10. C.-C. Wang M. M. L. Zulueta S.-C. Hung Chimia 2011 65 54 58
11. Y. Chapleur and F. Chétien, Preparative Carbohydrate Chemistry, ed. S. Hanessian, Marcel Dekker, New York, 1997, pp 207-262
12. J. Yoshima Adv. Carbohydr. Chem. Biochem. 1984 42 69 134
13. W. D. Celmer Pure Appl. Chem. 1971 28 413 454
14. S. Hanessian, Total Synthesis of Natural Products: The Chiron Approach, Pergamon Press, Oxford, 1983
15. B. Fraser-Reid Acc. Chem. Res. 1996 29 57 66
16. H. C. Hang C. R. Bertozzi J. Am. Chem. Soc. 2001 123 1242 1243
17. J. E. Jackman C. A. Fierke L. N. Tumey M. Pirrung T. Uchiyama S. H. Tahir O. Hindsgaul C. R. H. Raetz J. Biol. Chem. 2000 275 11002 11009
18. X. Li T. Uchiyama C. R. H. Raetz O. Hindsgaul Org. Lett. 2003 5 539 541
19. M. H. D. Postema, C-Glycoside Synthesis, CRC Press, Boca Raton, 1995
20. D. E. Levy and C. Tang, The Chemistry of C-Glycosides, Elsevier, Oxford, 1995
21. D. E. Kevy and P. Fügedi, The Organic Chemistry of Sugars, CRC Press, Boca Raton, 2006
22. S. Hanessian A. G. Pernet Adv. Carbohydr. Chem. Biochem. 1976 33 111 188
23. M. H. D. Postema Tetrahedron 1992 48 8545 8599
24. Y. Du R. J. Linhardt I. R. Vlahov Tetrahedron 1998 54 9913 9961
25. X. Yuan R. J. Linhardt Curr. Top. Med. Chem. 2005 5 1393 1430
26. N. K. Kochetkov L. I. Kudryashov A. P. Klyagina J. Gen. Chem., U.S.S.R., Engl. Ed. 1962 32 402 404
27. T. D. Inch G. J. Lewis Carbohydr. Res. 1970 15 1 10
28. J.-M. Beau S. Aburaki J.-R. Pougny P. Sinay J. Am. Chem. Soc. 1983 105 621 622
29. S. Challenger G. Procter Tetrahedron Lett. 1986 27 391 394
30. A. J. Wood D. J. Holt M.-C. Dominguez P. R. Jenkins J. Org. Chem. 1998 63 8522 8529
31. S. Hanessian G. Rancourt Pure Appl. Chem. 1977 49 1201 1214
32. C. Brockway P. Kocienski C. Pant J. Chem. Soc., Perkin Trans. 1 1984 875 878
33. G. Procter D. Genin Carbohydr. Res. 1990 202 81 92
34. S. Hanessian P. Dextraze Can. J. Chem. 1972 50 226 232
35. F. G. de las Heras A. S. Félix A. Calvo-Mateo P. Fernández-Resa Tetrahedron 1985 41 3867 3873
36. B. Fraser-Reid L. Magdzinski B. F. Molino D. R. Mootoo J. Org. Chem. 1987 52 4495 4504
37. M. I. Mangione A. G. Suárez R. A. Spanevello Carbohydr. Res. 2003 338 2177 2187
38. R. W. Scott C. M. Heathcock Carbohydr. Res. 1996 291 205 208
39. T. Linker K. Hartmann T. Sommermann D. Scheutzow E. Ruckdeschel Angew. Chem., Int. Ed. Engl. 1996 35 1730 1732
40. The Chemistry of the Cyclopropyl Group, ed., Z. Z. Rappoport, Wiley-VCH, Weinheim, 1996
41. H.-U. Reissig Top. Curr. Chem. 1988 144 73 135
42. J. R. Y. Salaün Top. Curr. Chem. 1988 144 1 71
43. Carbocyclic Three- and Four-membered Ring Compounds: v. e (Methods in Organic Chemistry), ed., A. D. Meijere, Thieme Publishing Group, 1996
44. S. Danishefsky Acc. Chem. Res. 1979 12 66 72
45. E. Wenkert Acc. Chem. Res. 1980 13 27 31
46. L. A. Paquette Chem. Rev. 1986 86 733 750
47. H. N. C. Wong M. Y. Hon C. W. Tse Y. C. Yip J. Tanko T. Hudlicky Chem. Rev. 1989 89 165 198
48. H. Lebel J. F. Marcoux C. Molinaro A. Charetter Chem. Rev. 2003 103 977 1050
49. L. K. Sydnes Chem. Rev. 2003 103 1130 1150
50. H.-U. Reissig R. Zimmer Chem. Rev. 2003 103 1151 1196
51. G. S. Cousins J. O. Hoberg Chem. Soc. Rev. 2000 29 165 174
52. B. Fraser-Reid B. J. Carthy Can. J. Chem. 1972 50 2928 2934
53. R. K. Boeckman A. B. Charette T. Asberom B. H. Johnston J. Am. Chem. Soc. 1987 109 7553 7555
54. M. K. Gurjar A. Chakrabarti B. Venkateswara Rao P. Kumar Tetrahedron Lett. 1997 38 6885 6888
55. P. Bertinato D. Meng A. Balog D. Su T. Kamenecka E. J. Sorensen S. J. Danishefsky J. Am. Chem. Soc. 1997 119 10073 10092
56. V. Samano M. J. Robins J. Am. Chem. Soc. 1992 114 4007 4008
57. K. J. Henry B. Fraser-Reid Tetrahedron Lett. 1995 36 8901 8904
58. C. M. Timmers M. A. Leeuwenburgh J. C. Verheijen G. A. van der Marel J. M. van Boom Tetrahedron: Asymmetry 1996 7 49 52
59. J. S. Brimacombe M. E. Evans E. J. Forbes A. B. Foster J. M. Webber Carbohydr. Res. 1967 4 239 243
60. G. F. Weber S. S. Hall J. Org. Chem. 1979 44 447 449
61. C. V. Ramana R. Murali M. Nagarajan J. Org. Chem. 1997 62 7694 7703
62. W. M. zu Reckendorf U. Kamprath-Scholtz Angew. Chem., Int. Ed. Engl. 1968 7 142 143
63. T. Sakakibara T. Takamoto R. Sudoh T. Hakagawa Chem. Lett. 1972 1219 1222
64. B. J. Fitzsimmons B. Fraser-Reid Tetrahedron 1984 40 1279 1287
65. M. Kawana H. Kuzuhara Synthesis 1995 544 552
66. C. Ramana M. Nagarajan Synlett 1997 763 764
67. R. Boeckman A. Charette T. Asberom B. Johnston J. Am. Chem. Soc. 1991 113 5337 5353
68. J. O. Hoberg D. J. Claffey Tetrahedron Lett. 1996 37 2533 2536
69. P. Bertinato E. J. Sorensen D. Meng S. J. Danishefsky J. Org. Chem. 1996 61 8000 8001
70. E. Fernandez-Megia S. Gourlaouen S. V. Ley G. J. Rowlands Synlett 1998 991 994
71. C. Ramana M. Nagarajan Carbohydr. Lett. 1998 3 117 119
72. P. R. Sridhar K. C. Ashalu S. Chandrasekaran Org. Lett. 2004 6 1777 1779
73. T. Sommermann B. G. Kim K. Peters E.-M. Peters T. Linker Chem. Commun. 2004 2624 2625
74. J. Yin T. Linker Org. Biomol. Chem. 2009 7 4829 4831
75. J. Yin T. Linker Tetrahedron 2011 67 2447 2461
76. S. D. Haveli P. R. Sridhar P. Suguna S. Chandrasekaran Org. Lett. 2007 9 1331 1334
77. P. R. Sridhar P. V. Kumar K. Seshadri R. Satyavathi Chem.-Eur. J. 2009 15 7526 7529
78. J. Beyer R. Madsen J. Am. Chem. Soc. 1998 120 12137 12138
79. J. Beyer P. R. Skaanderup R. Madsen J. Am. Chem. Soc. 2000 122 9575 9583
80. D. Clive S. Daigneault J. Org. Chem. 1991 56 3801 3814
81. H. Shao S. Ekthawatchai S.-H. Wu W. Zou Org. Lett. 2004 6 3497 3499
82. H. Shao S. Ekthawatchai C.-S. Chen S.-H. Wu W. Zou J. Org. Chem. 2005 70 4726 4734
83. Q. Tian L. Dong X. Ma L. Xu C. Hu W. Zou H. Shao J. Org. Chem. 2011 76 1045 1053
84. B. Giese, Radicals in Organic Synthesis: Formation of Carbon-Carbon Bonds, Pergamon Press, Oxford, 1986
85. J. Fossey, D. Lefort and J. Sorba, Free Radicals in Organic Chemistry, Wiley, Chichester, 1995
86. D. P. Curran, N. A. Porter and B. Giese, Stereochemistry of Radical Reactions, VCH, Weinheim, 1996
87. T. Linker and M. Schmittel, Radikale und Radikalionen in der Organischen Synthese, Wiley-VCH, Weinheim, 1998
88. Radicals in Organic Synthesis, ed., P. Renaud, and, M. P. Sibi, Wiley-VCH, Weinheim, 2001
89. S. Z. Zard, Radical Reactions in Organic Synthesis, Oxford University Press, New York, 2003
90. A. Gansäuer Radicals in Synthesis I and II, Top. Curr. Chem. 2006 263
91. B. Giese K. Gröninger Tetrahedron Lett. 1984 25 2743 2746
92. G. E. Keck E. J. Enholm J. B. Yates M. R. Wiley Tetrahedron 1985 41 4079 4094
93. B. Giese Pure Appl. Chem. 1988 60 1655 1658
94. B. Giese Angew. Chem., Int. Ed. Engl. 1989 28 969 980
95. R. J. Ferrier C.-K. Lee T. A. Wood J. Chem. Soc., Chem. Commun. 1991 690 691
96. J. Cossy S. Ibji Carbohydr. Res. 1996 291 189 196
97. O. Jarreton T. Skrydstrup J.-F. Espinosa J. Jiménez-Barbero J.-M. Beau Chem.-Eur. J. 1999 5 430 441
98. S. W. T. Choe M. E. Jung Carbohydr. Res. 2000 329 731 744
99. H. C. Hang C. R. Bertozzi J. Am. Chem. Soc. 2001 123 1242 1243
100. M. H. D. Postema J. L. Piper L. Liu J. Shen M. Faust P. Andreana J. Org. Chem. 2003 68 4748 4754
101. R. J. Ferrier N. Prasad J. Chem. Soc. C 1969 581 586
102. R. D. Dawe B. Fraser-Reid J. Chem. Soc., Chem. Commun. 1981 1180 1181
103. K. Inaba S. Matsumura S. Yoshikawa Chem. Lett. 1991 485 488
104. V. Nair J. Mathew Jaya Prabhakaran Chem. Soc. Rev. 1997 26 127 132
105. V. Nair L. Balagopal R. Rajan J. Mathew Acc. Chem. Res. 2004 37 21 30
106. V. Nair A. Deepthi Chem. Rev. 2007 107 1862 1891
107. V. Nair A. Deepthi Tetrahedron 2009 65 10745 10755
108. T. Linker T. Sommermann F. Kahlenberg J. Am. Chem. Soc. 1997 119 9377 9384
109. J. Yin T. Sommermann T. Linker Chem.-Eur. J. 2007 13 10152 10167
110. T. Linker J. Organomet. Chem. 2002 661 159 167
111. J. Yin J. Spindler T. Linker Chem. Commun. 2007 2712 2713
112. T. Linker D. Schanzenbach E. Elamparuthi T. Sommermann W. Fudickar V. Gyóllai L. Somsák W. Demuth M. Schmittel J. Am. Chem. Soc. 2008 130 16003 16010
113. V. Gyóllai D. Schanzenbach L. Somsák T. Linker Chem. Commun. 2002 1294 1295
114. B. G. Kim U. Schilde T. Linker Synthesis 2005 9 1507 1513
115. K. Hartmann B. G. Kim T. Linker Synlett 2004 15 2728 2731
116. E. Elamparuthi B. G. Kim J. Yin M. Maurer T. Linker Tetrahedron 2008 64 11925 11937
117. E. Elamparuthi T. Linker Org. Lett. 2008 10 1361 1364
118. E. Elamparuthi T. Linker Angew. Chem., Int. Ed. 2009 48 1853 1855
119. J. Yin T. Linker Chem.-Eur. J. 2009 15 49 52
120. O. Jiménez G. de La Rosa R. Lavilla Angew. Chem., Int. Ed. 2005 44 6521 6525
121. S. K. Yousuf D. Mukherjee L. Mallikharjunrao S. C. Taneja Org. Lett. 2011 13 576 579
122. S. R. Vidadala T. M. Pimpalpalle T. Linker S. Hotha Eur. J. Org. Chem. 2011 2426 2430
123. S. Kashyap S. Rao Vidadala S. Hotha Tetrahedron Lett. 2007 48 8960 8962
124. H.-M Liu F. Zhang D.-P. Zou Chem. Commun. 2003 2044 2045
125. A. Bari H. Feist D. Michalik M. Michalik K. Peseke Synthesis 2004 2863 2868
126. S. Norsikian A. Lubineau Org. Biomol. Chem. 2005 3 4089 4094
127. A. Lubineau Y. Canac N. Le Goff Adv. Synth. Catal. 2002 344 319 327
128. C. Jäkel K. H. Dötz Tetrahedron 2000 56 2167 2173
129. C. Mamat M. Hein R. Miethchen Carbohydr. Res. 2006 341 1758 1763
130. P. K. Kancharla Y. D. Vankar J. Org. Chem. 2010 75 8457 8464