Synthetic methodologies for C-nucleosides

Synthesis

Volumn , Issue 10, 2004, Pages 1533-1553

  Wu, Qinpei ^a,c   Simons, Claire ^b,c,d,e,f  

^a BEIJING INSTITUTE OF TECHNOLOGY   (China)

^b CARDIFF UNIVERSITY   (United Kingdom)

^c KING'S COLLEGE LONDON   (United Kingdom)

^d KARMANOS CANCER INSTITUTE   (United States)

^e UNIVERSITY OF LEICESTER   (United Kingdom)

^f CNRS   (France)

Author keywords

Anticancer; Antiviral; C nucleosides; Heck type reaction; Organometallic reagents

Indexed keywords

CONDENSATION; DERIVATIVES; DRUG DOSAGE; STEREOCHEMISTRY; SUGARS; SYNTHESIS (CHEMICAL);

ANTICANCER THERAPY; NUCLEOSIDES;

PROTEINS;

C NUCLEOSIDE; LACTONE DERIVATIVE; LEWIS ACID; NUCLEOSIDE DERIVATIVE; ORGANOMETALLIC COMPOUND;

CHEMICAL REACTION; DRUG SYNTHESIS; HECK REACTION; REACTION ANALYSIS; REVIEW; STEREOCHEMISTRY;

EID: 3142736550     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-829106     Document Type: Review

References (109)

1. Simons, C. Nucleoside Mimetics Their Chemistry and Biological Properties; Gordon and Breach Science Publishers: Australia, Canada, 2001.
2. Peasley, K. Medical Hypotheses 2000, 55, 408.
3. Townsend, L. B. Chemistry of Nucleosides and Nucleotides; Plenum Press: New York, 1994, 421-535.
4. Miller, P. S. Antisense/Antigene Oligonucleotides, In Bioorganic Chemistry-Nucleic Acids; Hecht, S. M., Ed.; Oxford University Press: New York and Oxford, 1996, 347-374.
5. Guntaka, R. V.; Varma, B. R.; Weber, K. T. Int. J. Biochem. Cell Biol. 2003, 55, 22.
6. Navarre, J.; Guianvarch, D.; Giorgio, A. F.; Condom, R.; Benhida, R. Tetrahedron Lett. 2003, 44, 2200.
7. Togo, H.; He, W.; Waki, Y.; Yokoyama, M. Synlett 1998, 700.
8. Shaban, A. E.; Nasr, A. Z. Adv. Heterocycl. Chem. 1998, 71, 164.
9. Shaban, A. E.; Nasr, A. Z. Adv. Heterocycl. Chem. 1997, 68, 225.
10. Lerch, U.; Burdon, M. G.; Moffatt, J. G. J. Org. Chem. 1968, 33, 140.
11. Brown, D. M.; Burdon, M. G. J. Chem. Soc. 1968, 1051.
12. Rabat, M. M.; Pankiewicz, K. W.; Watanabe, K. A. J. Med. Chem. 1987, 30, 924.
13. Alderweireldt, I.; Vrijens, E. L.; Esmans, E. L.; Wotring, L. L.; Townsend, L. B.; De Clercq, E. Nucleosides Nucleotides 1989, 8, 891.
14. Belmans, M.; Esmans, E.; Dommisse, R.; Lepoiver, J.; Alderweireldt, F.; Balzarini, J.; De Clercq, E. Nucleosides Nucleotides 1985, 4, 523.
15. Belmans, M.; Vrijens, I.; Esmans, E.; Dommisse, R.; Lepoiver, J.; Alderweireldt, F.; Townsend, L.; Wotring, J.; Balzarini, J.; De Clercq, E. Nucleosides Nucleotides 1986, 5, 441.
16. Yokoyama, M.; Toyoshima, A.; Akiba, T.; Togo, H. Chem. Lett. 1994, 265.
17. Yokoyama, M.; Akiba, T.; Togo, H. Synthesis 1995, 638.
18. Belmans, M.; Vrijens, I.; Esmans, E.; Dommisse, R.; Lepoiver, J.; Alderweireldt, F.; Townsend, L.; Wotring, J.; Balzarini, J.; De Clercq, E. Nucleosides Nucleotides 1989, 8, 307.
19. Joose, P. E.; Esmans, E. L.; Dommisse, R. A.; Lepiovre, J. A.; Aldeweireldt, F. C. Nucleosides Nucleotides 1991, 10, 323.
20. Joose, P. E.; Esmans, E. L.; Dommisse, R. A.; Van Dongen, W.; Lepiovre, J. A.; Aldeweireldt, F. C.; Balzarini, J.; De Clercq, E. Nucleosides Nucleotides 1991, 10, 883.
21. Joose, P. E.; Esmans, E. L.; Dommisse, R. A.; Brugh, A. D. E. W.; Balzarini, J.; De Clercq, E. Helv. Chim. Acta 1992, 75, 1613.
22. Solomon, M. S.; Hopkins, P. B. Tetrahedron Lett. 1991, 32, 3297.
23. Brown, D. M.; Ogden, R. C. J. Chem. Soc., Perkin Trans. 1 1981, 723.
24. Krohn, K.; Heins, H.; Wielckens, K. J. Med. Chem. 1992, 35, 511.
25. Yokoyama, M.; Tanabe, T.; Togo, H. Synthesis 1993, 517.
26. Harusawa, S.; Murai, Y.; Moriyama, H.; Imazu, T.; Ohishi, H.; Yoneda, R.; Kurihara, T. J. Org. Chem. 1996, 61, 4405.
27. Yokoyama, M.; Tanabe, T.; Togo, H. Chem. Lett. 1994, 265.
28. Chen, J. J.; Drach, J. C.; Townsend, L. B. J. Org. Chem. 2003, 68, 4170.
29. Reese, C. B.; Wu, Q. Org. Biomol. Chem. 2003, 1, 3160.
30. Yokoyama, M.; Toyoshima, H.; Shimizu, M.; Togo, H. J. Chem. Soc., Perkin Trans. 1 1997, 29.
31. Reese, C. B.; Wu, Q.; Capaldi, D. unpublished results.
32. Eaton, M. A.; Millican, A. T. J. Chem. Soc., Perkin Trans. 1 1988, 545.
33. Obika, S.; Hari, Y.; Mono, K.; Imanishi, T. Tetrahedron Lett. 2000, 41, 215.
34. Hari, T.; Obika, S.; Sakaki, M.; Mono, K.; Yamagata, Y.; Imanishi, T. Tetrahedron 2003, 58, 3051.
35. Obika, S.; Hari, Y.; Sugimoto, T.; Sekiguchi, M.; Imanishi, T. Tetrahedron Lett. 2000, 41, 8923.
36. Heck, R. F. Org. React. 1982, 27, 345.
37. Whitcombe, N.; Hii, K. K.; Gibson, S. E. Tetrahedron 2001, 57, 7449.
38. Arai, I.; Daves, G. D. J. Am. Chem. Soc. 1978, 100, 287.
39. Cheng, J. Y.-G.; Hacksell, U.; Daves, G. D. J. Org. Chem. 1986, 51, 3093.
40. Hacksell, U.; Daves, G. D. J. Org. Chem. 1983, 48, 2870.
41. Hsieh, H. P.; Mclaughlin, L. W. J. Org. Chem. 1995, 60, 5356.
42. Searls, T.; Chen, D. L.; Lan, T.; Mclaughlin, L. W. Biochemistry 2000, 4375.
43. Zhang, H. C.; Daves, G. D. Jr. J. Org. Chem. 1992, 57, 4690.
44. Zhang, H. C.; Daves, G. D. Jr. J. Org. Chem. 1993, 58, 2557.
45. Farr, R. N.; Kwok, D. I.; Daves, G. D. Jr. J. Org. Chem. 1992, 57, 2093.
46. Chen, D. L.; McLaughlin, L. W. J. Org. Chem. 2000, 65, 7468.
47. Liu, H.; Guo, J.; Maynard, L.; Saito, D.; Kool, E. T. J. Am. Chem. Soc. 2004, 126, 1102.
48. Liu, H.; Guo, J.; Lynch, S. R.; Saito, D.; Maynard, L.; Kool, E. T. Science 2003, 302, 868.
49. Li, J.; Fan, Y.; Zhang, Y.; Marky, L. A.; Gold, B. J. Am. Chem. Soc. 2003, 125, 2084.
50. Li, J.; Shikiya, R.; Marky, L. A.; Gold, B. Biochemistry 2004, 43, 1440.
51. Coleman, R.; Madaras, M. L. J. Org. Chem. 1998, 63, 5700.
52. Miles, R. W.; Tyler, P. C.; Evans, G. B.; Furneaux, R. H.; Parkin, D. W.; Schramm, V. L. Biochemistry 1999, 38, 13147.
53. Evans, G. B.; Furneaux, R. H.; Hutchison, T. L.; Kezar, H. S.; Morris, P. E. Jr.; Schramm, V. L.; Tyler, P. C. J. Org. Chem. 2001, 66, 5723.
54. Haberli, A.; Leumann, C. J. Org. Lett. 2001, 3, 489.
55. Gudmundsson, K. S.; Williams, J. D.; Drach, J. C.; Townsend, L. B. J. Med. Chem. 2003, 46, 1449.
56. Shapiro, R.; Chambers, R. W. J. Am. Chem. Soc. 1961, 83, 3920.
57. Mertes, M. P.; Zielinski, J.; Pillar, C. J. Med. Chem. 1967, 320.
58. Chaudhuri, N. C.; Kool, E. T. Tetrahedron Lett. 1995, 36, 1795.
59. Chen, D. W.; Beuscher, A. E. IV; Stevens, R. C.; Wirsching, P.; Lerner, R. A.; Janda, K. D. J. Org. Chem. 2001, 66, 1725.
60. Ren, R.; Chaudhuri, N. C.; Paris, P. L.; Rumney, P. S.; Kool, E. T. J. Am. Chem. Soc. 1996, 118, 7671.
61. Chaudhuri, N. C.; Ren, R. X.-F.; Kool, E. T. Synlett 1997, 341.
62. Pirrung, M. C.; Zhao, X.; Harris, S. V. J. Org. Chem. 2001, 66, 2067.
63. Strassler, C.; Davis, N. E.; Kool, E. T. Helv. Chem. Acta 1999, 82, 2160.
64. Beuck, C.; Singh, I.; Bhattacharya, A.; Hecker, W.; Parmar, V. S.; Seitz, O.; Weinhold, E. Angew. Chem. Int. Ed. 2003, 42, 3958.
65. Wang, Z. X.; Duan, W.; Wiebe, L. I.; Balzarini, J.; Clercq, E. D.; Knaus, E. E. Nucleosides Nucleotides 2001, 20, 11.
66. Piccirilli, J. A.; Krauch, T.; Macpherson, L. J.; Benner, S. A. Helv. Chim. Acta 1991, 397.
67. Liu, W.; Walker, J. A.; Chen, J. J.; Wise, D. S.; Townsend, L. B. Tetrahedron Lett. 1996, 37, 5325.
68. Liu, W.; Wise, D. S.; Townsend, L. B. J. Org. Chem. 2001, 66, 4783.
69. Joose, P. E.; Esmans, E. L.; De Clercq, E. Nucleosides Nucleotides 1991, 10, 853.
70. Hildbran, S.; Blaser, A.; Parel, S. P.; Leumann, C. J. J. Am. Chem. Soc. 1997, 119, 5499.
71. Brotschi, C.; Häberli, A.; Leumann, C. Angew. Chem. Int. Ed. 2001, 40, 3012.
72. Tanaka, K.; Shionoya, M. J. Org. Chem. 1999, 64, 5002.
73. Wichai, V.; Woski, S. A. Bioorg. Med. Chem. Lett. 1998, 3465.
74. Wichai, U.; Woski, S. A. Org. Lett. 1999, 1173.
75. Matulic-Adamic, J.; Beigelman. L. Tetrahedron Lett. 1997, 38, 204.
76. Matulic-Adamic, J.; Beigelman, L. Tetrahedron Lett. 1997, 38, 1669.
77. Gudmundsson, K. S.; Drach, J. C.; Townsend, L. B. Tetrahedron Lett. 1996, 37, 2365.
78. Gudmundsson, K. S.; Drach, J. C.; Townsend, L. B. J. Org. Chem. 1997, 62, 3453.
79. Asbun, W.; Binkley, S. B. J. Org. Chem. 1968, 31, 140.
80. Pankiewicz, K. W.; Sochacka, E.; Rabat, M. M.; Ciszewski, L. A.; Watanabe, K. A. J. Org. Chem. 1988, 53, 3473.
81. Pankiewicz, K. W.; Rabat, M. M.; Sochacka, E.; Ciszewski, L.; Zeidler, J.; Watanabe, A. K. Nucleosides Nucleotides 1988, 7, 389.
82. Ogara, H.; Takashi, H. J. Org. Chem. 1974, 37, 1374.
83. Kabat, M. M.; Pankiewicz, K. W.; Sochacka, E.; Watanabe, K. A. Chem. Pharm. Bull. Jpn. 1988, 36, 634.
84. Sollogoub, M.; Fox, K. R.; Powers, V. E.; Brown, T. Tetrahedron Lett. 2002, 43, 3121.
85. Rabat, M. M.; Pankiewiez, K. W.; Watanable, K. A. J. Med. Chem. 1987, 924.
86. Ogura, H.; Takahashi, H. J. Org. Chem. 1974, 39, 1374.
87. Pankiewiez, K. W.; Kabat, M. M.; Sochacka, E.; Ciszewski, L.; Zeidler, J.; Watanabe, A. K. Nucleosides Nucleotides 1988, 8, 589.
88. Verberckmoes, F. C.; Esmans, E. L.; Balzarini, J.; De Clerq, E. Nucleosides Nucleotides 1991, 10, 1771.
89. Alderweireldt, F.; Vrijens, I.; Esmans, E.; Wortring, J.; Townsend, L.; Balzarini, J.; De Clercq, E. Nucleosides Nucleotides 1988, 7, 891.
90. Verberckmoes, F. C.; Esmans, E. L.; Balzarini, J.; De Clerq, E. Nucleosides Nucleotides 1994, 13, 511.
91. Guianvarc'h, D.; Benhida, R.; Fourrey, J. L. Tetrahedron Lett. 2001, 42, 647.
92. Guianvarc'h, D.; Fourrey, J. L.; Huu Dau, M.; Guérineau, V.; Benhida, R. J. Org. Chem. 2002, 67, 3724.
93. Hanessian, S.; Machaalani, R. Tetrahedron Lett. 2003, 44, 8321.
94. Navarre, J.-M.; Guianvarc'h, D.; Farese-Di Giorgio, A.; Condon, R.; Benhida, R. Tetrahedron Lett. 2003, 44, 2199.
95. Yokoyama, M.; Ikenogami, T.; Togo, H. J. Chem. Soc., Perkin Trans. 1 2000, 2067.
96. Momotake, A.; Togo, H.; Yokoyama, M. J. Chem. Soc., Perkin Trans. 1 1999, 1193.
97. Diese, B.; Dupuis, J. Angew. Chem., Int. Ed. Engl. 1983, 22, 622.
98. Dupuis, J.; Diese, B.; Ruegge, D.; Fischer, H.; Korth, H. G.; Sustmann, R. J. Am. Chem. Soc. 1985, 107, 4332.
99. Girgis, N. S.; Michael, M. A.; Smee, D. F.; Alaghamandan, H. A.; Robins, R. K.; Cottam, H. B. J. Med. Chem. 1990, 33, 2750.
100. Farr, R. N.; Kwok, D. I.; Daves, G. D. Jr. J. Org. Chem. 1992, 2093.
101. Inoue, T.; Kuwujima, I. J. Chem. Soc., Chem. Commun. 1980, 251.
102. Rao, P.; Rao, K. V. B.; Otter, B. A.; Kelein, R. S.; Ren, W. Y. Tetrahedron Lett. 1988, 29, 3537.
103. Paul, S. A.; Otter, B. A.; Klein, R. S. J. Heterocycl. Chem. 1993, 509.
104. Mumper, M. W.; Aurenge, C.; Hosmane, R. S. Bioorg. Med. Chem. Lett. 1993, 3, 2847.
105. Stewart, A. O.; Williams, R. M. J. Am. Chem. Soc. 1985, 107, 4289.
106. Farkas, J.; Flegelova, Z.; Sorm, F. Tetrahedron Lett. 1972, 2279.
107. He, W.; Togo, H.; Yokoyama, M. Tetrahedron Lett. 1997, 5541.
108. Barton, D. H. R.; Ramesh, M. J. Am. Chem. Soc. 1990, 112, 891.
109. Mukaiyama, T.; Hirano, N.; Nishida, M.; Uchiro, H. Chem. Lett. 1997, 389.