Novel Bicylic Donors for the Synthesis of 2-Deoxy-β-Glycosides

Journal of Organic Chemistry

Volumn 63, Issue 7, 1998, Pages 2197-2208

  Franck, Richard W ^a   Marzabadi, Cecilia H ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 DEOXY BETA GLYCOSIDE; ANTINEOPLASTIC ANTIBIOTIC; GLYCOSIDE; MITHRAMYCIN; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; DRUG DNA BINDING; DRUG SYNTHESIS; GLYCOSYLATION; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY;

EID: 0032478668     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971934h     Document Type: Article

References (111)

1. Remers, W. A. In The Chemistry of Antitumor Antibiotics; Wiley-Interscience: New York, 1979; pp 133-175.
2. (b) Remers, W. A.; Iyengar, B. S. In Cancer Chemotherapeutic Agents; W. O. Foye, Ed.; American Chemical Society, 1995; p 578.
3. Lee, M. D.; Dunne, T. S.; Chang, C. C.; Siegel, M. M.; Morton, G. O.; Ellestad, G. A.; McGahren, W. J.; Borders, D. B. J. Am. Chem. Soc. 1992, 114, 985.
4. (b) Nicolau, K. C.; Dai, W. M. Agnew. Chem. Int. Ed. Engl. 1991, 30, 1387.
5. Henderson, F. G. In Digitalis; C. Fish and Surawicz, Eds.; Grune & Stratton; New York, 1969; pp 3-21.
6. Rohr, J.; Thiericke, P. Nat. Prod. Rep. 1992, 9, 103.
7. Thiem, J.; Klaffke, W. Top. Curr. Chem. 1990, 154, 285;
8. (b) Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503.
9. Gao, X.; Patel, D. J. Biochemistry 1989, 28, 751.
10. (b) Banville, D. L.; Keniry, M. A.; Shafer, R. H. Biochemistry 1990, 29, 6521.
11. (c) Ibid. Biochemistry 1990, 29, 9204.
12. (d) Gao, X.; Patel, D. J. Biochemistry 1990, 29, 10940.
13. (e) Gao, X.; Mirau, P.; Patel, D. J. J. Mol. Biol. 1992, 223, 259.
14. (f) Sastry, M.; Patel, D. J. Biochemistry 1993, 32, 6588.
15. Koshel, K.; Hartmann, G.; Kersten, W.; Kersten, H. Biochem. Z. 1966, 344, 76.
16. (b) Behr, W.; Honikel, K.; Hartmann, G. Eur. J. Biochem. 1969, 9, 82.
17. (c) Hayaska, T.; Inoue, Y. Biochemistry 1969, 8, 2342.
18. (a) Silva, D. J.; Goodnow, R.; Kahne, D. Biochemistry 1993, 32, 463.
19. (b) Silva, D. J.; Kahne, D. E. J. Am. Chem. Soc. 1993, 115, 7962.
20. Silva, D. J.; Kahne, D. J. Am. Chem. Soc. 1994, 116, 2641.
21. (a) Ramesh, S.; Franck, R. W. J. Chem. Soc., Chem. Commun. 1989, 960.
22. (b) Ramesh, S.; Kaila, N.; Grewal, G.; Franck, R. W. J. Org. Chem. 1990, 55, 5.
23. (c) Grewal, G.; Kaila, N.; Franck; R. W. J. Org. Chem. 1992, 57, 2084.
24. (d) Franck, R. W.; Kaila, N. Carbohydr. Res. 1993, 239, 71.
25. (a) Sebesta, D. P.; Roush, W. R. J. Org. Chem. 1992, 57, 4799.
26. (b) Roush, W. R.; Lin, X. J. Am. Chem. Soc. 1995, 117, 2236.
27. (c) Roush, W. R.; Briner, K.; Kesler, B. S.; Murphy, M. J. Org. Chem. 1996, 61, 6098.
28. A preliminary report of this work has appeared: Marzabadi, C. H.; Franck, R. W. J. Chem. Soc., Chem. Commun. 1996, 2651.
29. For examples see: (a) Koenigs, W.; Knorr, E. Chem. Ber. 1901, 34, 957. (b) Lemieux, R. U.; Hayami, J. L. Can. J. Chem. 1965, 43, 2162. (c) Paulsen, H.; Lockoff, O. Chem. Ber. 1981, 114, 3102.
30. For examples see: (a) Koenigs, W.; Knorr, E. Chem. Ber. 1901, 34, 957. (b) Lemieux, R. U.; Hayami, J. L. Can. J. Chem. 1965, 43, 2162. (c) Paulsen, H.; Lockoff, O. Chem. Ber. 1981, 114, 3102.
31. For examples see: (a) Koenigs, W.; Knorr, E. Chem. Ber. 1901, 34, 957. (b) Lemieux, R. U.; Hayami, J. L. Can. J. Chem. 1965, 43, 2162. (c) Paulsen, H.; Lockoff, O. Chem. Ber. 1981, 114, 3102.
32. (a) Mukaiyama, T.; Murai, Y.; Shoda, S. Chem. Lett. 1981, 431.
33. (b) Nicolau, K. C.; Dolle, R. E.; Papahatjis, D. P.; Randall, J. L. J. Am. Chem. Soc. 1984, 106, 4189.
34. (a) Helferich, B,; Shimitz-Hillebrecht, E. Chem. Ber. 1933, 66, 378.
35. (b) Lemeiux, R. U.; Shyluk, W. P. Can. J. Chem. 1953, 31, 528.
36. (c) Hanessian, S.; Banoub, J. Carbohydr. Res. 1977, 59, 261.
37. (d) Dahmen, J.; Frejd, T.; Magnusson, G.; Noori, G. Carbohydr. Res. 1983, 114, 328.
38. (e) Ogawa, T.; Beppu, K.; Nakabayashi, S. Carbohydr. Res. 1981, 93, C6.
39. (a) Ferrier, R. J.; Hay, R. W.; Vethaviyasar, N. Carbohydr. Res. 1983, 116, 162.
40. (b) Ito, Y.; Ogawa, T. Tetrahedron Lett. 1988, 29, 1061.
41. (c) Nicolau, K. C.; Seitz, S. P.; Papahatjis, D. P. J. Am. Chem. Soc. 1983, 105, 2430.
42. (d) Konradsson, P. Udodong, U. E.; Fraser-Reid, B. Tetrahedron Lett. 1990, 31, 4313.
43. (e) Veeneman, G. H.; van Leeuwen, S. H.; van Boom, J. H. Tetrahedron Lett. 1990, 31, 1331.
44. (f) Dasgupta, F.; Garegg, P. J. Carbohydr. Res. 1988, 177, C13.
45. (g) Fugedi, P.; Garregg, P. J. Carbohydr. Res. 1986, 149, C9.
46. Kahne, D.; Walker, S.; Chang, Y.; van Enger, D. J. Am. Chem. Soc. 1989, 111, 6881.
47. (a) Boger, D. L.; Honda, T. J. Am. Chem. Soc. 1994, 116, 5647.
48. (b) Kondo, H.; Aoki, S.; Ichikawa, Y.; Halcomb, R. L.; Ritzen, H.; Wong, C.-H., J. Org. Chem. 1994, 59, 864.
49. (c) Muller, T.; Schneider, R.; Schmidt, R. R. Tetrahedron Lett. 1994, 35, 4763.
50. (d) Watanabe, Y.; Nakamoto, C.; Yammamoto, S.; Ozaki, S. Tetrahedron 1994, 50, 6523.
51. (e) Yamanoi, T.; Nakamura, K.; Takeyama, H.; Yanagihara, Y. Bull. Chem. Soc. Jpn. 1994, 67, 1359.
52. (f) Muller, T.; Hummel G.; Schmidt, R. R.; Liebigs Ann. Chem. 1994, 325.
53. (g) Singh, K.; Fernandez-Mayorlas, A.; Martin-Lomas, M. J. Chem. Soc. Chem. Commun. 1994, 775.
54. Schmidt, R. R.; Michel, J. Agnew. Chem. Int. Ed. Engl. 1980, 19, 731.
55. (a) Fraser-Reid, B.; Konradsson, P.; Mootoo, D. R., Udodong, U. J. Chem. Soc., Chem. Commun. 1988, 823. (
56. b) Mootoo, D. R.; Konradsson, P.; Udodong, U.; Fraser-Reid, B. J. Am. Chem. Soc. 1988, 110, 5583.
57. (c) Mootoo, D. R.; Konradsson, P.; Fraser-Reid, B. J. Am. Chem. Soc. 1989, 111, 8540.
58. (a) Chenault, H. K.; Chafin, L. F. J. Org. Chem. 1994, 59, 6167.
59. (b) Chenault, H. K.; Castro, A.; Chafin, L. F.; Yang, J. J. Org. Chem. 1996, 61, 5024.
60. Marra, A.; Esnault, J.; Veyrieres, A.; Sinay, P. J. Am. Chem. Soc. 1992, 114, 6354.
61. de Raadt, A.; Ferrier, R. J. Carbohydr. Res. 1991, 216, 93.
62. (a) Boons, G. J.; Isles, S. Tetrahedron Lett. 1994, 35, 3593.
63. (b) Boons, G. J.; Isles, S. J. Org. Chem. 1996, 61, 4262.
64. Senaidman, M. L.; Johnson, S. C.; Crasto, C.; Hecht, S. M. J. Org. Chem. 1995, 60, 3942.
65. Vankar, Y. D.; Vankar, P. S.; Behrendt, M.; Schmidt, R. R. Tetrahedron 1991, 47, 9985.
66. (a) Deslongchamps, P. In Stereoelectronic Effects in Organic Chemistry; Pergammon Press: Oxford, 1983; pp 4-29.
67. (b) Kirby, A. J. The Anomeric Effect and Related Stereoelectronic Effects at Oxygen; Springer-Verlag: New York, 1983.
68. (c) Juaristi, E.; Cuevas, G. Tetrahedron 1992, 48, 5019.
69. Feather, M. S.; Harris, J. F. J. Org. Chem. 1965, 30, 153.
70. (a) Bock, K.; Pedersen, M.; Thiem, J. Carbohydr. Res. 1979, 73, 85.
71. (b) Thiem, J.; Gerken, M. J. Org. Chem. 1985, 50, 954.
72. (a) Thiem, J.; Gerken, M.; Schottmer, B.; Weigand, J. Carbohydr. Res. 1987, 164, 327.
73. (b) Thiem, J.; Schottmer, B. Agnew. Chem., Int. Ed. Engl. 1987, 26, 555.
74. (a) Nicolau, K. C.; Ladduwahetty, T.; Randal, J. L.; Chucholowski, A. J. Am. Chem. Soc. 1986, 108, 2466.
75. (b) Toshima, K.; Mukaiyama, S.; Ishiyama, T.; Tatsuta, K. Tetrahedron Lett. 1990, 31, 3339. See also ref 5b.
76. Perez, M.; Beau, J. M. Tetrahedron Lett. 1989, 30, 75.
77. Tavecchia, P.; Trumtel, M.; Veyieres, A.; Sinay, P. Tetrahedron Lett. 1989, 30, 2533.
78. Gupta, R. B.; Franck, R. W. J. Am. Chem. Soc. 1989, 111, 7668.
79. For example see: (a) Capozzi, G.; Nativi, C.; Menichetti, S.; Rosi, A.; Valle, G. Tetrahedron 1992, 48, 9023.
80. (b) Capozzi, G.; Menichetti, S.; Nativi, C.; Rossi, A.; Franck, R. W. Tetrahedron Lett. 1993, 34, 4253.
81. (c) Capozzi, G.; Franck, R. W.; Menichetti, S.; Mattioli, M.; Nativi, C.; Valle, G. J. Org. Chem. 1995, 60, 6416.
82. Ley, S. V.; Bombala, M. U. J. Chem. Soc., Perkin Trans. 1 1979, 3013.
83. (a) Presented in part: 209th National ACS Meeting, Anaheim, CA; April 1995; CARB 033.
84. (b) Presented in part: 211th National ACS Meeting, New Orleans, LA; March 1996; ORGN 300.
85. Capozzi, G.; Mannocci, F.; Menichetti, S.; Nativi, C.; Paoletti, S. J. Chem. Soc., Chem. Commun. 1997, 2291.
86. (a) Capozzi, G.; Dios, A.; Franck, R. W.; Geer, A.; Marzabadi, C.; Menichetti, S.; Nativi, C.; Tamarez, M. Agnew. Chem., Int. Ed. Engl. 1996, 35, 7.
87. Watson, A. T.; Park, K.; Wiemer, D. P.; Scott, W. J. J. Org. Chem. 1995, 60, 5102 and ref 17 therein.
88. Bock, K.; Pedersen, C. J. Chem. Soc., Perkin Trans. 2 1974, 293.
89. Bolitt, V.; Mioskowski, C.; Lee, S. G.; Falck, J. R. J. Org. Chem. 1990, 55, 5812.
90. Inanaga, J.; Yokoyama, Y.; Hanamoto, T. Tetrahedron Lett. 1993, 34, 2791.
91. Igarashi, K.; Irisawa, J.; Honma, T. Carbohydr. Res. 1975, 39, 213-225.
92. Marino-Albernas, J. R.; Bittman, R.; Peters, A.; Mayhew, E. J. Med. Chem. 1996, 39, 3241.
93. Dziewiszek, K.; Zamoiski, A. Carbohydr. Res. 1986, 150, 163.
94. Garegg, M. E. P. J.; Hultberg, H.; Oscarson, S. J. Carbohydr. Chem. 1983, 2, 305.
95. Marzabadi, C. H.; Spilling, C. D. J. Org. Chem. 1993, 58, 3761.
96. A similar debenzylation of a primary benzyloxy group has recently been reported: Pozgay, V.; Dubois, E. P.; Lotter, H.; Nezmelyi, A. Carbohydr. Res. 1997, 303, 165.
97. Silva, D. J.; Kraml, C. M.; Kahne, D. Biorg., & Med. Chem. 1994, 2, 1251.
98. Kometani, U.; Kondo, H.; Fujimori, Y. Synthesis 1988, 1005.
99. (a) Crich, D.; Ritchie, T. J. J. Chem. Soc., Chem. Commun. 1988, 1461.
100. (b) Crich, D.; Ritchie, T. Carbohydr. Res. 1989, 190, C1.
101. (c) Crich, D.; Ritchie, T. J. J. Chem. Soc., Perkins Trans. 1 1990, 945.
102. Hashimoto, S.; Yanagiya, Y.; Honda, T.; Ikegami, S. Chem. Lett. 1992, 1511.
103. Lemieux, R. U.; Hendriks, K. B.; Stick, R. V.; James, K. J. Am. Chem. Soc. 1975, 97, 4056.
104. (a) Crich, D.; Sun, S. J. Org. Chem. 1997, 62, 1198.
105. (b) While this manuscript was undergoing revision the existence of anomeric triflates as reactive intermediates was convincingly shown: Crich, D.; Sun, S. J. Am. Chem. Soc. 1997, 119, 11217.
106. Mozingo, R. Org. Synth. Coll. Vol. 3, 1955, 181.
107. Kozikowski, A. P.; Lee, J. J. Org. Chem. 1990, 55, 863.
108. Prepared by methanolysis of tri-O-acetyl-D-glucal using Amberlite IRA-400 resin.
109. Blackburne, I. D.; Fredericks, D. M.; Guthrie, R. D. Aust. J. Chem. 1976, 29, 381.
110. Danishefsky, S. J.; Behar, V.; Randolph, J. T.; Lloyd, K. O. J. Am. Chem. Soc. 1995, 117, 5701.
111. Fraser-Reid, B.; Walker, D. L.; Tam, Y.-K.; Holder, N. L. Can. J. Chem. 1973, 51, 3950.