Synthesis and partial biological evaluation of a small library of differentially-linked β-C-disaccharides

Journal of Organic Chemistry

Volumn 68, Issue 12, 2003, Pages 4748-4754

  Postema, Maarten H D ^a   Piper, Jared L ^a   Jie Shen, Lei Liu ^a   Faust, Marcus ^a   Andreana, Peter ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

PRECURSORS;

ACIDS; ENZYMES; OXIDATION; SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

ALCOHOL; ALKENE; BETA C DISACCHARIDE; DISACCHARIDE; GLYCAL; GLYCOSIDASE; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; CYTOTOXICITY; HYDROBORATION; OXIDATION; SYNTHESIS; TUMOR CELL LINE;

BETA-GLUCOSIDASE; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; DISACCHARIDES; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; KINETICS; MOLECULAR STRUCTURE; OXIDATION-REDUCTION; PRUNUS; STEREOISOMERISM; TUMOR CELLS, CULTURED;

EID: 0038617365     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030039x     Document Type: Article

References (83)

1. This paper is dedicated to Professor Carl R. Johnson on the occasion of his retirement from Wayne State University.
2. (a) Postema, M. H. D. C-Glycoside Synthesis, 1st ed.; CRC Press: Boca Raton, LA, 1995; p 379.
3. (b) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides, 1st ed.; Elsevier Science: Oxford, UK, 1995; Vol. 13, p 290.
4. Cleavage of the C-glycoside bond of some aryl C-glycosides is known; see: Kumazawa, T.; Kimura, T.; Matsuba, S.; Sato, S.; Onodera, J.-i. Carbohydr. Res. 2001, 334, 207-213 and references therein.
5. For reviews on C-glycoside synthesis, see: (a) Postema, M. H. D.; Calimente, D. C-Glycoside Synthesis: Recent Developments and Current Trends. In Glycochemistry: Principles, Synthesis and Applications; Wang, P. G., Bertozzi, C., Eds.; Marcel Dekker: New York, 2000; Chapter 4, pp 77-131.
6. (b) Du, Y.; Lindhardt, R. J. Tetrahedron 1998, 54, 9913-9959.
7. (c) Beau, J.-M.; Gallagher, T. Top. Curr. Chem. 1997, 187, 1-54.
8. (d) Nicotra, F. Top. Curr. Chem. 1997, 187, 55-83.
9. (e) Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700-717.
10. (f) Jaramillo, C.; Knapp, S. Synthesis 1994, 1-20.
11. (g) Herscovici, J.; Antonakis, K. Recent Developments in C-Glycoside Synthesis. In Studies in Natural Product Chemistry, Stereoselective Synthesis; Elsevier: New York, 1988; Vol. 10, Part F, pp 337-403.
12. Krohn, K.; Rohr, J. Top. Curr. Chem. 1997, 188, 127-195.
13. Rohr, J.; Thiericke, R. Nat. Prod. Rep. 1992, 103-137.
14. For a comprehensive review on the synthesis of C-saccharides, see: Liu, L.; McKee, M.; Postema, M. H. D. Curr. Org. Chem. 2001, 5, 1133-1167.
15. For previous approaches to the synthesis of 1,6-linked C- disaccharides, see: (a) Postema, M. H. D.; Piper, J. L. Tetrahedron Lett. 2002, 43, 7095-7099.
16. (b) Griffin, F. K.; Paterson, D. E.; Taylor, R. J. K. Angew Chem., Int. Ed. 1999, 38, 2939-2942.
17. (c) Leeuwenburgh, M. A.; Timmers, C. M.; van der Marel, G. A.; van Boom, J. H.; Mallet, J. M.; Sinaÿ, P. Tetrahedron Lett. 1997, 38, 6251-6254.
18. (d) Dondoni, A.; Zuurmond, H.; Boscarato, A. J. Org. Chem. 1997, 62, 8114-8124.
19. (e) Kobertz, W. K.; Bertozzi, C. R.; Bednarski, M. D. J. Org. Chem. 1996, 61, 1894-1895.
20. (f) Armstrong, R. W.; Sutherlin, D. P. Tetrahedron Lett. 1994, 35, 7743-7746.
21. (g) Martin, O. R.; Lai, W. J. Org. Chem. 1993, 58, 176-185.
22. (h) Vauzeilles, B.; Cravo, D.; Mallet, J.-M.; Sinaÿ, P. Synlett 1993, 522-524.
23. (i) Baumberger, F.; Vasella, A. Helv. Chim. Acta 1983, 66, 2210-2222.
24. (j) Rouzaud, D.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1983, 1353-1354.
25. For an iterative Wittig-type approach to β-(1→6)-linked Coligosaccharides, see: Dondoni, A.; Marra, A.; Mizuno, M.; Giovannini, P. P. J. Org. Chem. 2002, 67, 4186-4199.
26. For some synthetic approaches to C-disaccharides, see: (a) Postema, M. H. D.; Calimente, D.; Liu, L.; Behrmann, T. L. J. Org. Chem. 2000, 65, 6061-6068.
27. (b) Griffin, F. K.; Paterson, D. E.; Taylor, R. J. K. Angew Chem., Int. Ed. 1999, 38, 2939-2942.
28. (c) Khan, N.; Cheng, X.; Mootoo, D. R. J. Am. Chem. Soc. 1999, 121, 4918-4919.
29. (d) Leeuwenburgh, M. A.; Timmers, C. M.; van der Marel, G.; van Boom, J. H.; Mallet, J. M.; Sinaÿ, P. Tetrahedron Lett. 1997, 38, 6251-6254.
30. (e) Dondoni, A.; Zuurmond, H.; Boscarato, A. J. Org. Chem. 1997, 62, 8114-8124.
31. (f) Mallet, A.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593-2608.
32. (g) Sutherlin, D. P.; Armstrong, R. W. J. Org. Chem. 1997, 62, 5267-5283.
33. (h) Martin, O. R.; Lai, W. J. Org. Chem. 1993, 58, 176-185.
34. (a) Wei, A.; Haudrechy, A.; Audin, C.; Jun, H.-S.; Haudrechy-Bretel, N.; Kishi, Y. J. Org. Chem. 1995, 60, 2160-2169.
35. (b) Asensio, J. L.; Espinosa, J. F.; Dietrich, H.; Cañada, F. J.; Schmidt, R. R.; Martin-Lomas, M.; André, S.; Gabius, H.-J.; Jiménez-Barbero, J. J. Am. Chem. Soc. 1999, 121, 8995-9000.
36. (c) Rubinstenn, G.; Sinaÿ, P.; Berthault, P. J. Chem. Phys. A 1997, 101, 2536-2540 and references therein.
37. Espinosa, J. F.; Montero, E.; Vian, A.; Garcia, J. L.; Dietrich, H.; Schmidt, R. R.; Martin-Lomas, M.; Imberty, A.; Cañada, F. J.; Jiménez-Barbero, J. J. Am. Chem. Soc. 1998, 120, 1309-1318 and references therein.
38. (a) Wei, A.; Boy, K. M.; Kishi, Y. J. Am. Chem. Soc. 1995, 117, 9432-9436.
39. (b) Wang, J.; Kovac, P.; Sinaÿ, P.; Glaudemans, C. P. J. Carbohydr. Res. 1998, 308, 191-193.
40. (c) Tsuruta, O.; Yuasa, H.; Kurono, S.; Hashimoto, H. Bioorg. Med. Chem. Lett. 1999, 9, 807-810.
41. (d) Yang, G.; Franck, R. W.; Bittman, R.; Samadder, P.; Arthur, G. Org. Lett. 2001, 3, 197-200.
42. Glycochemistry. Principles, Synthesis and Applications; Wang, P. G., Bertozzi, C. R., Eds.; Marcel Dekker Inc.: New York, 2001.
43. A portion of this work has been communicated in preliminary form: Liu, L.; Postema, M. H. D. J. Am. Chem. Soc. 2001, 123, 8602-8603.
44. Postema, M. H. D.; Calimente, D. J. Org. Chem. 1999, 64, 1770-1771.
45. Postema, M. H. D.; Calimente, D.; Liu, L.; Behrmann, T. L. J. Org. Chem. 2000, 65, 6061-6068.
46. Postema, M. H. D.; Calimente, D. Tetrahedron Lett. 1999, 40, 4755-4759.
47. Takai, K.; Kakiuchi, T.; Kataoka, Y.; Utimoto, K. J. Org. Chem. 1994, 59, 2668-2670.
48. For reviews on olefin metathesis chemistry, see: (a) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
49. (b) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012-3043.
50. (c) Wright, D. L. Curr. Org. Chem. 1999, 3, 211-240.
51. (d) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
52. (e) Ivin, K. J. J. Mol. Catal. A-Chem. 1998, 133, 1-16.
53. (f) Randall, M. L.; Snapper, M. L. J. Mol. Catal. A-Chem. 1998, 133, 29-40.
54. (g) Armstrong, S. K. J. Chem. Soc., Perkin Trans. 1 1998, 371-388.
55. (h) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
56. (i) Fürstner, A. Top. Catal. 1997, 4, 285-299.
57. (j) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452.
58. (k) Schmalz, H.-G. Angew. Chem., Int. Ed. Engl. 1995, 34, 1833-1836.
59. (a) Hanessian, S.; Martin, M.; Desai, R. C. J. Chem. Soc., Chem. Commun. 1986, 926-927.
60. (b) Schmidt, R. R.; Preuss, R.; Betz, R. Tetrahedron Lett. 1987, 28, 6591-6594.
61. Zheng, W.; DeMattei, J. A.; Wu, J. P.; Duan, J. J. W.; Cook, L. R.; Oinuma, H.; Kishi, Y. J. Am. Chem. Soc. 1996, 118, 7946-7968.
62. Keck, G. E.; Enholm, E. J.; Yates, J. B.; Wiley, M. R. Tetrahedron 1985, 41, 4079-4094.
63. Garegg, P. J.; Hultberg, H.; Wallin, S. Carbohydr. Res. 1982, 108, 97-101.
64. Mootoo, D.; Wilson, P.; Jammalamadaka, V. J. Carbohydr. Chem. 1994, 13, 841-849.
65. Koch, K.; Chambers, R. J. Carbohydr. Res. 1993, 241, 295-299.
66. Garegg, P. J.; Samuelsson, B. J. Chem. Soc., Perkin Trans. 1 1980, 2866-2869.
67. See Supporting Information.
68. Bal, B. S.; Childers, W. E., Jr.; Pinnick, H. W. Tetrahedron 1981, 37, 2091-2096.
69. Szeja, W. Carbohydr. Res. 1983, 115, 240-242.
70. Barton, D. H. R.; Jaszberenyi, J. C. Tetrahedron Lett. 1989, 30, 2619-2622.
71. Chen, S.-H.; Horvath, R. F.; Joglar, J.; Fisher, M. J.; Danishefsky, S. J. J. Org. Chem. 1991, 56, 5834-5845.
72. Lewis, M. D.; Cha, J. K.; Kishi, Y. J. Am. Chem. Soc. 1982, 104, 4976-4978.
73. Hosomi, A.; Sakata, Y.; Sakurai, H. Tetrahedron Lett. 1984, 25, 2383-2386.
74. Kajihara, Y.; Kodama, H.; Endo, T.; Hashimoto, H. Carbohydr. Res. 1998, 306, 361-378.
75. Freeman, F.; Robarge, K. D. Carbohydr. Res. 1987, 171, 1-11.
76. (a) Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875-3886.
77. (b) Feldman, J.; Murdzek, J. S.; Davis, W. M.; Schrock, R. R. Organometallics 1989, 8, 2260-2265.
78. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
79. Haudrechy, A.; Sinaÿ, P. J. Org. Chem. 1992, 57, 4142-4151.
80. Lourens, G. J.; Koekemoer, J. M. Tetrahedron Lett. 1975, 3719-3722.
81. Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335-10336.
82. We thank Dr. Frederick Valeriote of the Josephine Ford Cancer Center for carrying out these assays.
83. Corbett, T. H.; Valeriote, F. A.; Polin, L.; Panchapor, C.; Pugh, S.; White, K.; Lowichick, N.; Knight, J.; Bissery, M.-C.; Wozniak, A.; LoRusso, P.; Biernat, L.; Polin, D.; Knight, L.; Biggar, S.; Looney, D.; Demchick, L.; Jones, J.; Jones, L.; Blair, S.; Palmewr, K.; Essenmacher, S.; Lisow, L.; Mattes, L. C.; Cavenaugh, P.; Rake, J.; Baker, L. In Cytotoxic Anticancer Drugs: Models and Concepts for Drug Discovery and Development; Kluwer Academic Publishers: Boston, MA, 1992; pp 35-87.