Palladium-assisted routes to nucleosides

Chemical Reviews

Volumn 103, Issue 5, 2003, Pages 1875-1916

  Agrofoglio, Luigi A ^a   Gillaizeau, Isabelle ^a   Saito, Yoshio ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CATALYSIS; CHEMICAL MODIFICATION; COMPLEXATION; DNA; MOLECULAR STRUCTURE; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ACHIRAL LIGANDS; ALLYLIC ALKYLATION; CHIRAL LIGANDS; HECK REACTION; NUCLEOTIDES; PRINS REACTION; SONOGASHIRA REACTION; STILLE REACTION; SUZUKI MIYAURA REACTION; TSUJI TROST REACTION;

PALLADIUM COMPOUNDS;

LIGAND; NUCLEOSIDE; PALLADIUM;

ALKYLATION; CATALYSIS; CHEMISTRY; CYCLIZATION; REVIEW; SYNTHESIS;

ALKYLATION; CATALYSIS; CYCLIZATION; LIGANDS; NUCLEOSIDES; PALLADIUM;

EID: 0037944068     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr010374q     Document Type: Article

References (450)

1. (a) Yokoyama, M.; Momotake, A. Synthesis 1999, 1541.
2. (b) Borthwick, A. D.; Biggadike, K. Tetrahedron 1992, 48, 571.
3. (c) Agrofoglio, L. A.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, R. A.; Guedi, R. Tetrahedron 1994, 50, 10611.
4. (d) Akella, L. B.; Vince, R. Tetrahedron 1996, 52, 2789.
5. (e) Ferrero, M.; Gotor, V. Chem. Rev. 2000, 100, 4319.
6. (f) Zemlicka, J. Pharmacol. Ther. 2000, 85, 251.
7. (g) Agrofoglio, L. A.; Challand, S. R. Acyclic, Carbocyclic and L-Nucleosides; Kluwer Academic Publishers: Dordrecht, 1998.
8. (h) Ichikawa, E.; Kato, K. Synthesis 2002, 1.
9. (i) Ichikawa, E.; Kato, K. Curr. Med. Chem. 2001, 8, 385.
10. (j) Huryn, D. M.; Okabe, M. Chem. Rev. 1992, 92, 1745.
11. (a) Schaeffer, H. J.; Beauchamp, L.; De Miranda, P.; Elion, G.; Bauer, D. J.; Collins, P. Nature 1978, 272, 583.
12. (b) Elion, G. B.; Furman, P. A.; Fyfe, J. A.; De Miranda, P.; Beauchamp, L.; Schaeffer, H. J. Proc. Natl. Acad. Sci. U.S.A. 1977, 74, 5716.
13. (c) Furman, P. A.; St. Clair, M. H.; Fyfe, J. A.; Rideout, J. L.; Keller, P. M.; Elio, G. B. J. Virol. 1979, 32, 72.
14. (a) Heck, R. F. J. Am. Chem. Soc. 1968, 90, 5518.
15. (b) Heck, R. F. Palladium reagents in organic synthesis; Academic Press Inc.: Orlando, 1985.
16. (c) Heck, R .F. J. Am. Chem. Soc. 1968, 90, 5531.
17. (d) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry; Pergamon Press: New York, 2000.
18. Ruth, J. L.; Bergstrom, D. E. J. Org. Chem. 1978, 43, 2870.
19. Bergstrom, D. E.; Ruth, J. L. J. Am. Chem. Soc. 1976, 98, 1587.
20. Bergstrom, D. E.; Ruth, J. L.; Warwick, P. J. Org. Chem. 1981, 46, 432.
21. Cookson, R. C.; Dudfield, P. J. Eur. J. Med. Chem. 1985, 20, 375.
22. (a) Stevenson, T. M.; Bhanu Prasad, A. S.; Rao Citineni, J.; Knochel, P. Tetrahedron Lett. 1996, 37, 8375.
23. (b) Negishi, E.-I. J. Organomet. Chem. 2002, 653, 1.
24. Zhang, H.-C.; Daves, G. D. J. Org. Chem. 1993, 58, 2557.
25. (a) Trost, B. M.; Van Vranken, D. L. Chem. Rev. 1996, 96, 395.
26. (b) Trost, B. M. Acc. Chem. Res. 1996, 29, 355.
27. Trost, B. M.; Kuo, G.-H.; Benneche, T. J. Am. Chem. Soc. 1988, 110, 621.
28. Walkup, R. D.; Mosher, M. D. Tetrahedron Lett. 1994, 35, 8545.
29. Tsuji, J.; Yamakawa, T. Tetrahedron Lett. 1979, 20, 613.
30. (a) Mustafin, A. G.; Gataullin, R. R.: Abdrakhmanov, I. B.; Tolstikov, G. A. Bashk. Khim. Zh. 1996, 3, 4.
31. (b) Daves, G. D. Carbohydrates 1992, 49.
32. (c) Korshun, V. A.; Manasova, E. V.; Berlin, Y. A. Russ. J. Bioorg. Chem. 1997, 23, 300.
33. (d) Bergstrom, D. E. Nucleosides Nucleotides 1982, 1, 1.
34. Woltermann, C. J. J. PharmaChem. 2002, 1, 11.
35. Kumada, M. Pure Appl. Chem. 1980, 52, 669.
36. Negishi, E. Acc. Chem. Res. 1982, 15, 340.
37. Casey, C. P.; Whiteker, G. T. Isr. J. Chem. 1990, 30, 299.
38. Freer, R.; Geen, G. R.; Ramsay, T. W.; Share, A. C.; Slater, G. R.; Smith, N. M. Tetrahedron 2000, 56, 4589.
39. Tolman, C. A. J. Am. Chem. Soc. 1970, 92, 2953.
40. (a) Morrison, J. D. Asymmetric Synthesis; Academic Press: New York, 1983-1985; Vols. 1-5.
41. (b) Kočovský, P.; Tureček, F.; Hájíček, J. Synthesis of Natural Products: Problems of Stereoselectivity; CRC Press: Boca Raton, FL, 1986; Vols. 1 and 2.
42. (c) Nogrady, M. Stereoselective Synthesis; VCH: Weinheim, 1987.
43. (d) Ojima, I. Asymmetric Catalysis; VHC: New York, 1993.
44. (e) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley & Sons: New York, 1994.
45. (f) Dawson, G. J.; Bower, J. F.; Williams, J. M. J. Contemp. Org. Synth. 1996, 3, 277.
46. (g) Tonks, L.; Williams, J. M. J. Contemp. Org. Synth. 1997, 4, 353.
47. Rosini, C.; Franzini, L.; Raffaelli, A.; Salvadori, P. Synthesis 1992, 503.
48. For overviews on Pd(0)-catalyzed allylic substitution, see: (a) Frost, C. G.: Howarth, J.; Williams, J. M. Tetrahedron: Asymmetry 1992, 3, 1089.
49. (b) Starý, I.; Záji7acute;ček, J.; Kočovský, P. Tetrahedron 1992, 48, 7229.
50. (c) Williams, J. M. Synlett 1996, 705.
51. For asymmetric allylic substitutions using Pd-BINAP catalyst, see: (a) Trost, B. M.; Murphy, D. J. Organometallics 1985, 4, 1143.
52. (b) Fiaud, J. C.; Legros, J. Y. J. Organomet. Chem. 1989, 370, 383.
53. (c) Fiaud, J. C.; Legros, J. Y. J. Org. Chem. 1990, 55, 4840.
54. (d) Yamaguchi, M.; Shima, T.; Yamagishi, T.; Hida, M. Tetrahedron Lett. 1990, 31, 5049.
55. (e) Pregosin, P. S.; Ruegger, H.; Salzmann, R.; Albinati, A.; Lianza, F.; Kunz, R. W. Organometallics 1994, 13, 83.
56. (f) Legros, J. Y.; Fiaund, J. C. Tetrahedron 1994, 50, 465.
57. Sonogashira, K. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, p 521.
58. (a) Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467.
59. (b) Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627.
60. (c) Ratovelomana, V.; Linstrumelle, G. Synth. Commun. 1981, 11, 917.
61. (a) Cassar, L. J. Organomet. Chem. 1975, 93, 253.
62. (b) Dieck, H. A.; Heck, R. F. J. Organomet. Chem. 1975, 93, 259.
63. Sonogashira, K.; Yatake, T.; Tohda, Y.; Takahashi, S.; Hagihara, N. Chem. Commun. 1977, 291.
64. Alami, M.; Ferri, F.; Liastrumelle, G. Tetrahedron Lett. 1993, 34, 6403.
65. Robins, M. J.; Vinayak, R. S.; Wood, S. G. Tetrahedron Lett. 1990, 31, 3731.
66. Crisp, G. T.; Robertson, T. A. Tetrahedron 1992, 48, 3239.
67. (a) Farina, V.; Krishman, B. J. Am. Chem. Soc. 1991, 113, 9585.
68. (b) Casado, A. L.; Espinet, P. J. Am. Chem. Soc. 1998, 120, 8978.
69. (a) Stille, J. K. Angew. Chem., Int. Ed. Engl. 1986, 25, 508
70. (b) Stille, J. K. Angew. Chem. 1986, 98, 504
71. (c) Stille, J. K. Pure Appl. Chem. 1985, 57, 1771.
72. Mitchell, T. N. Synthesis 1992, 803.
73. Kosugi, M.; Sasazawa, K.; Shimuzi, Y.; Migita, T. Chem. Lett. 1977, 301.
74. Scott, W. J.; Stille, J. K. J. Am. Chem. Soc. 1986, 108, 3033.
75. Piers, E.; Friesen, R. W.; Keay, B. A. Tetrahedron 1991, 47, 4555.
76. Beletskaya, I. P. J. Organomet. Chem. 1983, 250, 551.
77. (a) Suzuki, A. Acc. Chem. Res. 1982, 15, 178
78. (b) Suzuki, A. Pure Appl. Chem. 1984, 66, 213
79. (c) Suzuki, A. Pure Appl. Chem. 1985, 57, 1749
80. (d) Suzuki, A. Pure Appl. Chem. 1991, 63, 419
81. (e) Suzuki, A. J. Organomet. Chem. 1999, 576, 147.
82. (a) Snieckus, V. Chem. Rev. 1990, 90, 879.
83. (b) Matteson, D. S. Tetrahedron 1989, 45, 1859.
84. (c) Chemler, S. R.; Trauner, D.; Danishefsky, S. Angew. Chem., Int. Ed. 2001, 40, 4544.
85. (a) Miyaura, N.; Suzuki, A. Chem. Commun. 1979, 866.
86. (b) Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437.
87. (c) Miyaura, N.; Yanagi, T.; Suzuki, A. Synth. Commun. 1981, 11, 513.
88. (a) Miyaura, N.; Yamada, K.; Suginome, H.; Suzuki, A. J. Am. Chem. Soc. 1985, 107, 972.
89. (b) Miyaura, N.; Sato, M.; Suzuki, A. Tetrahedron Lett. 1986, 27, 3745
90. (c) Miyaura, N.; Sato, M.; Suzuki, A. Chem. Lett. 1986, 1329.
91. (d) Ishiyama, T.; Miyaura, N.; Suzuki, A. Chem. Lett. 1987, 25.
92. (e) Miyaura, N.; Ishiyama, T.; Sasaki, H.; Ishiyama, M.; Sato, M.; Suzuki, A. J. Am. Chem. Soc. 1989, 111, 314.
93. Mizoroki, T.; Mori, K.; Ozaki, A. Bull. Chem. Soc. Jpn. 1971, 44, 581.
94. Julia, M.; Duteil, M. Bull. Soc. Chim. Fr. 1973, 2791.
95. (a) Sawamura, M.; Ito, Y. Chem. Rev. 1992, 92, 857.
96. (b) Kingsbury, C. L.; Mehrman, S. J.; Takacs, J. M. Curr. Org. Chem. 1999, 3, 497.
97. (c) Larsen, R. D. Curr. Opin. Drug Discovery Dev. 1999, 2, 651.
98. (d) Biffis, A.; Zecca, M.; Basato, M. J. Mol. Catal. A: Chem. 2001, 173, 249.
99. (a) Amatore, C.; Jutand, A.; M'Barki, M. Organometallics 1995, 14, 1818.
100. (b) Cavri, W.; Candiani, I.; Bedeschi, A. J. Org. Chem. 1992, 57, 3558.
101. (a) Trost, B. M.; Verhoeven, T. R. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.: Pergamon Press: New York, 1982; Vol. 8, Chapter 57.
102. (b) Trost, B. M. Acc. Chem. Res. 1980, 13, 385.
103. (c) Trost, B. M. Angew. Chem., Int. Ed. Engl. 1989, 28, 1173.
104. (d) Godleski, S. A. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.: Pergamon Press: New York, 1991; Vol. 4, Chapter 3.3.
105. (e) Fiaud, J. C. Asymmetric Catalysis in Organic Synthesis; J. Wiley: New York, 1994; Chapter 2.
106. (f) Tsuji, J.; Minami, I. Acc. Chem. Res. 1987, 20, 140.
107. (g) Consiglio, G.; Waymouth, R. M. Chem. Rev. 1989, 89, 257.
108. (h) Tsuji, J. Palladium Reagents and Catalysis; John Wiley & Sons: Chichester, 1995.
109. (i) Harrington, P. J. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press: New York, 1995; Vol. 12, Chapter 8.2.
110. (j) Moreno-Maňas, M.; Pleixats, R. Adv. Heterocycl. Chem. 1996, 96, 73.
111. (k) Tsuji, J. Palladium Reagents and Catalysts: Innovations in Organic Synthesis; Wiley: New York, 1995.
112. (a) Tsuji, J. Tetrahedron 1986, 42, 4361.
113. (b) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y. Tetrahedron Lett. 1982, 23, 4809.
114. (c) Tsuji, J.; Shimizu, I.; Minami, I.; Ohashi, Y.; Sugiura, T.; Takahashi, K. J. Org. Chem. 1985, 50, 1523.
115. (a) Hata, G.; Takahashi, K.; Miyake, A. Chem. Commun. 1970, 1392
116. (b) Hata, G.; Takahashi, K.; Miyake, A. Bull. Chem. Soc. Jpn. 1972, 45, 230.
117. (c) Tsuji, J.; Kobayashi, Y.; Kataoka, H.; Takahashi, T. Tetrahedron Lett. 1980, 21, 1475.
118. (a) Tsuji, J.; Kataoka, H.; Kobayashi, Y. Tetrahedron Lett. 1981, 22, 2575.
119. (b) Trost, B. M.; Molander, G. A. J. Am. Chem. Soc. 1981, 103, 5969.
120. (a) Collins, D. J.; Jackson, W. R.; Timms, R. N. Tetrahedron Lett. 1976, 17, 495
121. (b) Collins, D. J.; Jackson, W. R.; Timms, R. N. Aust. J. Chem. 1977, 30, 2167.
122. (c) Trost, B. M.; Weber, L. J. Am. Chem. Soc. 1975, 97, 1611.
123. (d) Trost, B. M.; Weber, L.; Strege, P. E.; Fullerton, T. J.; Dietsche, T. J. Am. Chem. Soc. 1976, 100, 3416.
124. (e) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1978, 100, 3435
125. (f) Trost, B. M.; Verhoeven, T. R. J. Am. Chem. Soc. 1980, 102, 4730
126. (g) Trost, B. M.; Verhoeven, T. R. J. Org. Chem. 1976, 41, 3215.
127. (g) Hayashi, T.; Hagihara, T.; Konishi, M.; Kumada, M. J. Am. Chem. Soc. 1983, 105, 7767.
128. (h) Hayashi, T.; Konishi, M.; Kumada, M. Chem. Commun. 1984, 107.
129. (i) Akermak, B.; Backwall, J. E.; Lowenborg, A.; Zetterberg, K. J. Organomet. Chem. 1979, 166, C33.
130. (j) Akermark, B.; Jutand, A. J. Organomet. Chem. 1981, 217, C41.
131. (k) Van Haaren, R. J.; Keeven, P. H.; Van der Veen, L. A.; Goubitz, K.; Van Strijdonck, G. P. F.; Oevering, H.; Reek, J. N. H.; Kamer, P. C. J.; Van Leeuwen, P. W. N. Inorg. Chim. Acta 2002, 327, 108.
132. (a) Hayashi, T.; Yamamoto, A.; Hagishara, T. J. Org. Chem. 1986, 51, 723.
133. (b) Fiaud, J. C.; Legros, J. Y. J. Org. Chem. 1987, 52, 1907.
134. Hoke, M. E.; Brescia, M.-R.; Bogaczyk, S.; DeShong, P.; King, B. W.; Crimmins, M. T. J. Org. Chem. 2002, 67, 327.
135. Trost, B. M. Chem. Pharm. Bull. 2002, 50, 1.
136. Trost, B. M.; Kallander, L. S. J. Org. Chem. 1999, 64, 5427.
137. (a) Trost, B. M.; Van Vranken, D. L.; Bingel, C. J. Am. Chem. Soc. 1992, 114, 9327.
138. (b) Trost, B. M.; Van Vranken, D. L. Angew. Chem., Int. Ed. Engl. 1992, 31, 228.
139. Hayashi, T.; Ohno, A.; Lu, S.-J.; Matsumoto, Y.; Fukuyo, E.; Yanaga, K. J. Am. Chem. Soc. 1994, 116, 4221.
140. For annual summaries of chiral ligands for induction of asymmetry into Pd-catalyzed reactions of allylic substrates, see: (a) Hegedus, L. S. Coord. Chem. Rev. 2000, 204, 199
141. (b) Hegedus, L. S. Coord. Chem. Rev. 1999, 175, 159
142. (c) Hegedus, L. S. Coord. Chem. Rev. 1998, 168, 49
143. (d) Hegedus, L. S. Coord. Chem. Rev. 1997, 161, 129
144. (e) Hegedus, L. S. Coord. Chem. Rev. 1996, 147, 443.
145. Trost, B. M.; Shi, Z. J. Am. Chem. Soc. 1996, 118, 3037.
146. Elming, N.; Claason-Kaas, N. Acta Chem. Scand. 1952, 6, 535.
147. Acevedo, O. L.; Andrews, R. S.; Dunkel, M.; Dan Cook, P. J. Heterocycl. Chem. 1994, 31, 989.
148. Vorbrüggen, H.; Krolikiewicz, K. Angew. Chem. 1976, 21, 724.
149. (a) De Clercq, E. Exp. Clin. Pharmacol. 1980, 2, 253.
150. (b) De Clercq, E. Biochem. Pharmacol. 1984, 33, 2159.
151. (a) De Clercq, E.; Descamp, J.; DeSomer, P.; Barr, P. J.; Jones, A. S.; Walker, R. T. Proc. Natl. Acad. Sci. U.S.A. 1979, 76, 2947.
152. (b) De Clercq, E.; Dewcamps, J.; Verhelst, G.; Walker, R. T.; Jones, A. S.; Torrence, P. F.; Shugar, D. J. Infect. Dis. 1980, 141, 563.
153. (c) Kundu, N. G.; Dasgupta, S. K. J. Chem. Soc., Perkin Trans. 1 1993, 2657.
154. Goodchild, J.; Porter, R. A.; Raper, R. H.; Sim, I. S.; Upton, R. M.; Viney, J.; Wadsworth, H. J. J. Med. Chem. 1983, 26, 1252.
155. Crisp, G.; Flynn, B. L. J. Org. Chem. 1993, 58, 6614.
156. (b) Bleackley, R. C.; Jones, A. S.; Walker, R. T. Tetrahedron 1976, 32, 2795.
157. (a) McGuigan C.; Yarnold, C. J.; Jones, G.; Velasquez, S.; Barucki, H.; Brancale, A.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. J. Med. Chem. 1999, 42, 4479.
158. (b) Barucki, H.; Blewett, S.; Carangio, A.; Ericschen, J. T.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. J. Med. Chem. 2000, 43, 4993.
159. (c) Srinivasan, S.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Bioorg. Med. Chem. Lett. 2001, 11, 391.
160. (d) McGuigan, C.; Brancale, A.; Barucki, H.; Srinivasan, S.; Jones, G.; Pathirana, R.; Blewett, S.; Alvarez, R.; Yarnold, C. J.; Carangio, A.; Velazquez, S.; Andrei, G.; Snoeck, R.; De Clercq, E. Drugs Future 2000, 25, 1151.
161. (e) Carangio, A.; McGuigan, C.; Andrei, G.; Snoeck, R.; De Clercq, E.; Balzarini, J. Antivir. Chem. Chemother. 2001, 12, 187.
162. Mansour, T. S.; Evans, C. A.; Charron, M.; Korba, B. E. Bioorg. Med. Chem. Lett. 1997, 7, 303.
163. (a) Robins, M. J.; Barr, P. J. J. Org. Chem. 1983, 48, 1854
164. (b) Robins, M. J.; Barr, P. J. Tetrahedron Lett. 1981, 22, 421.
165. Castro, C. E.; Gaughan, E. J.; Owsley, D. C. J. Org. Chem. 1966, 31, 4071.
166. Imamura, K-I.; Yamamoto, Y. Bioorg. Med. Chem. Lett. 1996, 6, 1855.
167. (a) Yamamoto, Y.; Seko, T.; Nakamura, H.; Nemoto, H.; Hojo, H.; Mukai, N.; Hashimoto, Y. J. Chem. Soc., Chem. Commun. 1992, 157.
168. (b) Schinazi, R. F.; Prusoff, W. H. J. Org. Chem. 1985, 50, 841.
169. (a) Prober, J. M.; Trainor, G. L.; Dam, R. J.; Hobbs, F. W.; Robertson, C. W.; Zagursky, R. J.; Cocuzza, A. J.; Jensen, M. A.; Baumeister, K. Science 1987, 238, 336.
170. (b) Langer, P. R.; Waldrop, A. A.; Ward, D. C. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 6633.
171. Hobbs, F. W. J. Org. Chem. 1989, 54, 3420.
172. (a) Miyasaka, T.; Tanak, H.; Baba, M.; Hayakawa, H.; Walker, R. T.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1989, 32, 2507.
173. (b) Baba, M.; Tanaka, H.; De Clercq, E.; Pauwels, R.; Balzarini, J.; Schols, D.; Nakashima, H.; Perno, C.-F.; Walker, R. T.; Miyasaka, T. Biochem. Biophys. Res. Commun. 1989, 165, 1375.
174. (a) Tanaka, H.; Baba, M.; Hayakawa, H.; Sakamaki, T.; Miyasaka, T.; Ubasawa, M.; Takashima, H.; Sekiya, K.; Nitta, I.; Shigeta, S.; Walker, R. T.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1991, 34, 349.
175. (b) Tanaka, H.; Haraguchi, K.; Oizumi, Y.; Fukui, M.; Miyasaka, T. Can. J. Chem. 1986, 64, 1560.
176. Farina, V.; Hauck, S. I. Synlett 1991, 157.
177. Herdewijn, P.; Kerremans, L.; Wigerinck, P.; Vandendriessche, F.; Van Aerschot, A. Tetrahedron Lett 1991, 32, 4397.
178. Pereyre, M.; Quintard, J.-P.; Rahm, A. Tin in Organic Synthesis; Butterworth & Co., Publ.: London, 1987.
179. Rahim, S. G.; Trivedi, N.; Bogunovic-Batchelor, M. V.; Hardy, G. W.; Mills, G.; Selway, J. W. T.; Snowden, W.; Littler, E.; Coe, P. L.; Basnak, I.; Whale, R. F.; Walker, R. T. J. Med. Chem. 1996, 39, 789.
180. (a) Reist, E. J.; Gueffroy, D. E.; Goodman, L. J. Am. Chem. Soc. 1964, 86, 5685.
181. (b) Bobek, M.; Whistler, R. L.; Bloch, A. J. Med. Chem. 1972, 15, 168.
182. (c) Dyson, M. R.; Coe, P. L.; Walker, R. T. J. Med. Chem. 1991, 34, 2782.
183. Eaborn, C.; Waters, J. A. J. Chem. Soc. 1962, 1131.
184. (a) Crisp, G. T. Synth. Commun. 1989, 19, 2117.
185. (b) Crisp, G. T.; Macolino, V. Synth. Commun. 1990, 20, 413.
186. Crisp, G. T.; Flynn, B. L. Tetrahedron Lett. 1990, 31, 1347.
187. Yamamoto, Y.; Seko, T.; Nemoto, H. J. Org. Chem. 1989, 54, 4734.
188. Laio, T. K.; Podrebarac, E. G.; Cheng, C. C. J. Am. Chem. Soc. 1964, 86, 1869.
189. (a) Bergstrom, D. E.; Ogawa, M. K. J. Am. Chem. Soc. 1978, 100, 8106.
190. (b) Bergstrom, D. E.; Beal, P.; Jenson, J.; Lin, X. J. Org. Chem. 1991, 56, 5598.
191. (c) Langer, P. R.; Waldrop, A. A.; Ward, D. Proc. Natl. Acad. Sci. U.S.A. 1981, 78, 6633.
192. (d) Dreyer, G. B.; Dervan, P. B. Proc. Natl. Acad. Sci. U.S.A. 1985, 82, 968.
193. (e) Telser, J.; Cruickshank, K. A.; Schanze, K. S.; Netzel, T. L. J. Am. Chem. Soc. 1989, 111, 7221.
194. (f) Bashkin, J. K.; Gard, J. K.; Modak, A. S. J. Org. Chem. 1990, 55, 5125.
195. (g) Iverson, B. L.; Dervan, P. B. J. Am. Chem. Soc. 1987, 15, 7823.
196. Whale, R. F.; Coe, P. L.; Walker, R. T.; Nucleosides Nucleotides 1991, 10, 1615.
197. (a) Itaya, T.; Shimomichi, M.; Ozasa, M. Tetrahedron Lett. 1988, 29, 4129.
198. (b) RajBhandary, U. L.; Faulkner, R. D.; Stuart, A. J. Biol. Chem. 1968, 243, 575.
199. (c) Thiebe, R.; Zachau, H. G. Eur. J. Biochem. 1968, 5, 546.
200. (d) Itaya, T. Chem. Pharm. Bull. 1987, 35, 4372.
201. (a) Hatanaka, Y.; Hiyama, T. Synlett 1991, 845.
202. (b) Hatanaka, Y.; Hiyama, T. Pure Appl. Chem. 1994, 66, 1471.
203. (c) Denmark, S. E.; Wang, Z. Synthesis 2000, 999.
204. (d) Hanamoto, T.; Kobayashi, T.; Kondo, M. Synlett 2001, 2, 281.
205. Matsuhashi, H.; Hatanaka, Y.; Kuroboshi, M.; Hiyama, T. Heterocycles 1996, 42, 375
206. Schroeder, A. C.; Bloch, A.; Perlman, J. L.; Bobek, M. J. Med. Chem. 1982, 25, 1255.
207. Tanaka, H.; Takashima, H.; Ubasawa, M.; Sekiya, K.; Nitta, I.; Baba, M.; Shigeta, S.; Walker, R. T.; De Clercq, E.; Miyasaka, T. J. Med. Chem. 1992, 35, 337.
208. (a) Hobbs, J. B. In Comprehensive Medicinal Chemistry; Sammes, P. G., Vol. Ed.; Pergamon Press: Oxford, UK, 1990; Vol. 2, pp 299-331.
209. (b) Jacobson, K. A. In Comprehensive Medicinal Chemistry; Emmet, J. C., Vol. Ed.; Pergamon Press: Oxford, UK, Vol. 3, pp 601-642.
210. (a) Kundu, N. G.; Das, P. J. Chem. Soc., Chem. Commun. 1995, 99.
211. Minn, K. Synlett 1991, 115.
212. Manfredini, S.; Baraldi, P. G.; Bazzanini, R.; Marangoni, M.; Simoni, D.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1995, 38, 199.
213. Palmisano, G.; Santagostino, M. Tetrahedron 1993, 49, 2533.
214. Jacobson, K. A.; van Galen, P. J. M.; Williams, M. J. Med. Chem. 1992, 35, 407.
215. (a) De Clercq, E. J. Med. Chem. 1986, 29m 1561.
216. (b) Mitsuya, H.; Broder, S. Proc. Natl. Acad. Sci. U.S.A. 1986, 83, 1911.
217. (a) Nair, V.; Wiechert, R. J. Bioorg. Chem. 1980, 9, 423.
218. (b) Wong, C. G.; Meyer, R. B. J. Med. Chem. 1984, 27, 429.
219. (c) Rawn, J. D. Biochemistry; Harper and Row: New York 1983; pp 929-978.
220. Matsuda, A.; Shinozaki, M.; Yamaguchi, T.; Homma, H.; Nomoto, R.; Miyasaka, T.; Watanabe, Y.; Abiru, T. J. Med. Chem. 1992, 35, 241.
221. (a) Echavarren, A. M.; Stille, J. K. J. Am. Chem. Soc. 1988, 110, 1557.
222. (b) Ohe, T.; Miyaura, N.; Suzuki, A. J. Org. Chem. 1993, 58, 2201.
223. Adah, S. A.; Nair, V. Tetrahedron 1997, 53, 6747.
224. (a) Nair, V.; Turner, G. A.; Buenger, G. S.; Chamberlain, S. D. J. Org. Chem. 1988, 53, 3051.
225. (b) Nair, V.; Buenger, G. S. Synthesis 1988, 848.
226. (c) Nair, V.; Turner, G. A.; Chamberlain, S. D. J. Am. Chem. Soc. 1987, 109, 7223.
227. (d) Nair, V.; Lyons, A. G. Tetrahedron 1989, 45, 3653.
228. Van Aerschot, A. A.; Mamos, P.; Weyns, N. J.; Ikeda, S.; De Clercq, E.; Herdewijn, P. A. J. Med. Chem. 1993, 36, 2938.
229. Robins, M. J.; Hatfield, P. W.; Balzarini, J.; De Clercq, E. J. Med. Chem. 1984, 27, 1486.
230. Lang, P.; Magnin, G.; Mathis, G.; Burger, A.; Biellmann, J.-F. J. Org. Chem. 2000, 65, 7825.
231. Cong-Danh, N.; Beaucourt, J. P.; Pichat, L. Tetrahedron Lett. 1979, 20, 3159.
232. Tanaka, H.; Uchida, Y.; Shinozaki, M.; Hayakawa, H.; Matsuda, A.; Miyasaka, T. A. Chem. Pharm. Bull. 1983, 31, 787.
233. Ueda, T.; Nomoto, Y.; Matsuda, A. Chem. Pharm. Bull. 1985, 33, 3263.
234. Sági, G.; Ötvös, L.; Ikeda, S.; Andrei, G.; Snoeck, R.; De Clercq, E. J. Med. Chem. 1994, 37, 1307.
235. Koyama, S.; Kumazawa, Z.; Kashimura, N. Nucleic Acids Symp. Ser. 1982, 11, 41.
236. Crisp, G. T.; Gore, J. Tetrahedron 1997, 53, 1523.
237. Volpini, R.; Costanzi, S.; Lambertucci, C.; Vittori, S.; Klotz, K.-N.; Lorenzen, A.; Cristalli, G. Bioorg. Med. Chem. Lett. 2001, 11, 1931.
238. (a) Poulsen, S.-A.; Quinn, R. J. Bioorg. Med. Chem. 1998, 6, 619.
239. (b) Williams, M.; Jarvis, M. F. Biochem. Pharmacol. 2000, 59, 1173.
240. Montgomery, J. A.; Hewson, K. J. J. Med. Chem. 1968, 11, 48.
241. Yamane, A.; Matsuda, A.; Ueda, T. Chem. Pharm. Bull. 1980, 28, 150.
242. (a) Tabone, J. C.; Stamm, M. R.; Gamper, H. B.; Meyer, R. B. Biochemistry 1994, 33, 375.
243. (b) Coleman, R. S.; Kesicki, E. A. J. Org. Chem. 1995, 60, 6252.
244. (c) Chatterjee, M.; Rokita, S. E. J. Am. Chem. Soc. 1994, 116, 1690.
245. Nagatsugi, F.; Uemura, K.; Nakashima, S.; Maeda, M.; Sasaki, S. Tetrahedron 1997, 53, 3035.
246. Langli, G.; Gundersen, L. L.; Rise, F. Tetrahedron 1996, 52, 5625.
247. Gundersen, L.-L. Acta Chem. Scand. 1996, 50, 58.
248. Ozola, V.; Persson, T.; Gronowitz, S.; Hörnfeldt, A.-B. J. Heterocycl. Chem. 1995, 32, 863.
249. Malm, J.; Björk, P.; Gronowitz, S.; Hörnfeldt, A.-B Tetrahedron Lett. 1994, 35, 3195.
250. Gronowitz, S.; Björk, P.; Malm, J.; Hörnfeldt, A.-B. J. Organomet. Chem. 1993, 460, 127.
251. (a) Mamos, P.; Van Aerschot, A. A.; Weyns, N. J.; Herdewijn, P. A. Tetrahedron Lett. 1992, 33, 2413.
252. (b) Tu, C.; Keane, C.; Eaton, B. E. Nucleosides Nucleotides 1995, 14, 1631.
253. (c) Tu, C.; Eaton, B. PCT Int. Appl. WO 9616972, 1996; Chem. Abstr. 1996, 125, 143238.
254. (d) Moriarty, R. M.; Epa, W. R.; Awasthi, A. K. Tetrahedron Lett. 1990, 31, 5877.
255. (a) Havelková, M.; Hocek, M.; Česnek, M.; Dvořák, D. Synlett 1999, 1145.
256. (b) Hocek, M.; Holý, A.; Votruba, I.; Dvořáková, H. J. Med. Chem. 2000, 43, 1817.
257. (c) Hocek, M.; Holý, A.; Votruba, I.; Dvořákovǎ, H. Collect. Czech. Chem. Commun. 2000, 65, 1683.
258. Hocek, M.; Holý, A.; Votruba, I.; Dvořáková, H. Collect. Czech. Chem. Commun. 2001, 66, 483.
259. Česnek, M.; Hocek, M.; Holý, A. Collect. Czech. Chem. Commun. 2000, 65, 1357.
260. Lakshman, M. K.; Hilmer, J. H.; Martin, J. Q.; Keeler, J. C.; Dinh, Y. Q. V.; Ngass, F. N.; Russon, L. M. J. Am. Chem. Soc. 2001, 123, 7779.
261. Lakshman, M. K.; Thomson, P. F.; Nuqui, M. A.; Hilmer, J. H.; Sevova, N.; Boggess, B. Org. Lett. 2002, 4, 1479.
262. Amann, N.; Wagenknecht, H.-A. Synlett 2002, 5, 687.
263. For instance, see: (a) Jean, J. M.; Hall, K. B. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 37.
264. (b) Kawai, M.; Lee, M. J.; Evans, K. O.; Nordlund, T. M. J. Fluoresc. 2001, 11, 23.
265. (c) Wagenknecht, H.-A.; Rajski, S. R.; Pascaly, M.; Stemp, E. D.; Barton, J. K. J. Am. Chem. Soc. 2001, 123, 4400.
266. (d) Hess, S.; Götz, M.; Davis, W. B.; Michel-Beyerle, M.-E. J. Am. Chem. Soc. 2001, 123, 10046.
267. Williams, T. T.; Odom, D. T.; Barton, J. K. J. Am. Chem. Soc. 2000, 122, 9048.
268. (a) Rosemeyer, H.; Zulauf, M.; Ramzaeva, N.; Becher, G.; Feiling, E.; Mühlegger, K.; Münster, I.; Lohmann, A.; Seela, F. Nucleosides Nucleotides 1997, 16, 821.
269. (b) Seela, F.; Zulauf, M. Chem.-Eur. J. 1998, 4, 1781.
270. Seela, F.; Zulauf, M.; Sauer, M.; Deimel, M. Helv. Chim. Acta 2000, 83, 910.
271. (a) Guzaev, A.; Salo, H.; Azhayev, A.; Lönnberg, H. Bioconjugate Chem. 1996, 7, 240.
272. (b) Uhlmann, E.; Peyman, A. Chem. Rev. 1990, 90, 543.
273. (c) Goodchild, J. Bioconjugate Chem. 1990, 1, 165.
274. (d) Beaucage, S. L.; Iyer, R. P. Tetrahedron 1993, 49, 1925.
275. Seela, F.; Zulauf, M. J. Chem. Soc., Perkin Trans. 1 1998, 3233.
276. (a) Zhang, L.; Zhang, Y.; Li, X.; Zhang, L. Bioorg. Med. Chem Lett. 2002, 10, 907.
277. (b) Suhadolnik, R. J. Nucleoside Antibiotics; Wiley-Interscience: New York, 1970; Chapter 8, p 315.
278. (c) Suhadolnik, R. J. Nucleosides as Biological Probes; Wiley-Interscience: New York, 1979; Chapter 3, p 158.
279. (d) Shih, C.; Hu, Y. Tetrahedron Lett. 1994, 35, 4677.
280. (e) Edstrom, E. D.; Wei, Y. J. Org. Chem. 1995, 60, 5069.
281. Seela, F.; Zulauf, M. Synthesis 1995, 726.
282. (a) Rosemeyer, H.; Seela, F. Helv. Chim. Acta 1988, 71, 1573.
283. (b) Anderson, J. D.; Bontems, R. J.; Geary, S.; Cottam, H. B.; Larson, S. B.; Matsumoto, S. S.; Smee, D. F.; Robins, R. K. Nucleosides Nucleotides 1989, 8, 1201.
284. Seela, F.; Zulauf, M.; Chen, S.-F. Nucleosides, Nucleotides Nucleic Acids 2000, 19, 237.
285. (a) Ramzaeva, N.; Mittelbach, C.; Seela, F. Helv. Chim. Acta 1997, 80, 1809.
286. (b) Seela, F.; Becher, G. Helv. Chim. Acta 1999, 82, 1640.
287. (c) Seela, F.; Zulauf, M. Helv. Chim. Acta 1999, 82, 1878.
288. (a) Streetter, D. G.; Witkowski, J. T.; Khare, G. P.; Sidwell, R. W.; Bauer, R. J.; Robins, R. K.; Simon, L. N. Proc. Natl. Acad. Sci. U.S.A. 1973, 70, 1174.
289. (b) Riley, T. A.; Larson, S. B.; Avery, T. L.; Finch, R. A.; Robins, R. K. J. Med. Chem. 1990, 33, 572.
290. (c) Srivastava, P. C.; Pickering, M. V.; Allen, L. B.; Streeter, D. G.; Campbell, M. T.; Witkowski, J. T.; Sidwell, R. W.; Robins, R. K. J. Med. Chem. 1977, 20, 256.
291. (d) Smith, A. R.; Sidwell, R. W.; Robins, R. K. Annu. Rev. Pharmacol. Toxicol. 1980, 20, 259.
292. (e) Mizuno, K.; Tsujino, M.; Takada, M.; Hayashi, M.; Atsumi, K.; Asano, K.; Matsuda, T. J. Antibiot. 1974, 27, 775.
293. (a) Minakawa, N.; Takeda, T.; Sasaki, T.; Matsuda, A.; Ueda, T. J. Med. Chem. 1991, 34, 778.
294. (b) Manfredini, S.; Bazzanini, R.; Baraldi, P. G.; Simoni, D.; Vertuani, S.; Pani, A.; Pinna, E.; Scintu, F.; Lichino, D.; La Colla, P. Bioorg. Med. Chem. Lett. 1996, 6, 1279.
295. Aoyagi, M.; Minakawa, N.; Matsuda, A. Tetrahedron Lett. 1993, 34, 103.
296. Song, Y.-L.; Morin, C. Synlett 2001, 266
297. (a) Neumann, H. G. J. Cancer Res. Clin. Oncol. 1986, 112, 100.
298. (b) Beland, F. A.; Kadlubar, F. F. Environ. Health Perspect. 1985, 62, 19.
299. Kool, E. T.; Morales, J. C.; Guckian, K. M. Angew. Chem., Int. Ed. 2000, 39, 990.
300. Wood, R. D.; Mitchell, M.; Sgouros, J.; Lindahl, T. Science 2001, 291, 1284.
301. (a) Hartwig, J. F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2046.
302. (b) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
303. (c) Hartwig, J. F. Acc. Chem. Res. 1998, 31, 852.
304. (d) Frost, C. G.; Mendonça, P. J. Chem. Soc., Perkin Trans. 1 1998, 2615.
305. (a) Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215.
306. (b) Driver, M. S.; Hartwig, J. F. J. Am. Chem. Soc. 1996, 118, 7217.
307. (c) Mercoux, J.-F.; Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1568.
308. (d) Mann, G.; Hartwig, J. F.; Driver, M. S.; Fernandez-Rivas, C. J. Am. Chem. Soc. 1998, 120, 827.
309. (e) Sadighi, J. P.; Harris, M. C.; Buchwald, S. L. Tetrahedron. Lett. 1998, 39, 5327.
310. (f) Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367.
311. Lakshman, M. K. J. Organomet. Chem. 2002, 653, 234.
312. Wang, Z.; Rizzo, C. J. Org. Lett. 2001, 3, 565.
313. Old, D. W.; Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1999, 121, 10453.
314. Meier, C.; Gräsl, S. Synlett 2002, 5, 802.
315. Schoffers, E.; Olsen, P. D.; Means, J. C. Org. Lett. 2001, 3, 4221.
316. Tu, C.; Keane, C.; Eaton, B. Nucleosides Nucleotides 1997, 16, 227.
317. For examples on the displacement of the halides from the C-6 position, see: Srivastava, P. C.; Robins, R. K.; Meyer, R. B. In Chemistry of Nucleosides and Nucleotides; Townsend, L. B., Ed.; Plenum Press: New York, 1998; Chapter 2, pp 113-280.
318. Lakshman, M. K.; Keeler, J. C.; Hilmer, J. H.; Martin, J. Q. J. Am. Chem. Soc. 1999, 121, 6090.
319. Wagaw, S.; Buchwald, S. L. J. Org. Chem. 1996, 61, 7240.
320. De Riccardis, F.; Bonala, R. R.; Johnson, F. J. Am. Chem. Soc. 1999, 121, 10453
321. De Riccardis, F.; Johnson, F. Org. Lett. 2000, 2, 293.
322. Harwood, E. A.; Sigurdsson, S. T.; Edfelt, N. B. F.; Reid, B. R.; Hopkins, P. B. J. Am. Chem. Soc. 1999, 121, 5081.
323. Jones, M.; Roberts, S. J. Chem. Soc., Perkin Trans. 1 1988, 2927.
324. (a) Agrofoglio, L. A.; Challand, S. R. In Acyclic, Carbocyclic and L-Nucleosides; Kluwer Academic Publishers: Dordrecht, 1998; pp 174-284.
325. (b) Marquez, V.; Lim, M. Med. Res. Rev. 1986, 6, 1.
326. (c) Roberts, S.; Biggadike, K.; Borthwick, A.; Kirk, B. In Topics in Medicinal Chemistry; Leeming, P. R., Ed.; Royal Society of Chemistry: London, 1988; p 172.
327. (d) Crimmins, M. Tetrahedron 1998, 54, 9229.
328. (a) Tseng, C.; Marquez, V.; Fuller, R.; Goldstein, B.; Haines, D.; McPherson, H.; Parsons, J.; Shannon, W.; Arnett, G.; Hollingshead, M.; Driscoll, J. J. Med. Chem. 1989, 32, 1442.
329. (b) Marquez, V.; Bodenteich, M.; Copp, R.; Lim, B. Nucleic Acids Res., Symp. Ser. 1990, 22, 35.
330. Wolfe, M.; Anderson, B.; Borcherding, D.; Borchardt, R. J. Org. Chem. 1990, 5, 4712.
331. Kapeller, H.; Marschner, C.; Weissenbacher, M.; Griengl, H. Tetrahedron 1998, 54, 1439.
332. (a) Vorbrüggen, H.; Krolikiewicz, K.; Bennua, B. Chem. Ber. 1981, 114, 1234.
333. (b) Vorbrüggen, H.; Hofle, G. Chem. Ber. 1981, 114, 1256.
334. (a) Gundersen, L.-L.; Benneche, T.; Undheim, K. Tetrahedron. Lett. 1992, 33, 1085.
335. (b) Gundersen, L.-L.; Benneche, T.; Rise, F.; Gogoll, A.; Undheim, K. Acta Chem. Scand. 1992, 46, 761.
336. (c) Coe, D. M.; Roberts, S. M.; Storer, R. J. Chem. Soc., Perkin Trans. 1 1992, 20, 2695.
337. Deardorff, D. R.; Myles, D. C.; MacFerrin, K. D. Tetrahedron Lett. 1985, 26, 5615.
338. Deardorff, D. E.; Shulman, M. J.; Sheppeck, J. E. Tetrahedron Lett. 1989, 30, 6625.
339. Peel, M. R.; Sternbach, D. D.; Johnson, M. R. J. Org. Chem. 1991, 56, 4990.
340. Coe, D. M.; Hilpert, H.; Noble, S. A.; Peel, M. R.; Roberts, S. M.; Storer, R. J. Chem. Soc., Chem. Commun. 1991, 312.
341. Arnau, N.; Cortés, J.; Moreno-Mañas, M.; Pleixats, R.; Villaroya, M. J. Heterocycl. Chem. 1997, 34, 233.
342. Hildbrand, S.; Leumann, C.; Scheffold, R. Helv. Chim. Acta 1996, 79, 702.
343. (a) Deardorff, D. R.; Shambayati, S.; Linde, R. G.; Dunn, M. M. J. Org. Chem. 1988, 53, 189.
344. (b) Larock, R. C.; Lee, N. H. Tetrahedron Lett. 1991, 32, 6315.
345. (a) Cheng, P. T. W.; McLean, S. Can. J. Chem. 1989, 67, 261.
346. (b) Larock, R. C.; Lee, N. H. Tetrahedron Lett. 1991, 32, 5911.
347. (c) Kalck-Pedersen, M. L.; Benneche, T.; Undheim K. Acta Chem. Scand. 1993, 47, 72.
348. (a) Siddiqi, S. M.; Chen, X.; Schneller, S. W. Nucleosides Nucleotides 1993, 12, 267.
349. (b) Siddiqi, S. M.; Chen, X.; Rao, J.; Schneller, S. W. J. Med. Chem. 1995, 38, 1035.
350. (c) Koga, M.; Schneller, S. W. J. Org. Chem. 58, 6471.
351. (d) Hedge, V. R.; Seley, K. L.; Schneller, S. W. J. Heterocycl. Chem. 2000, 37, 1361.
352. Johnson, C. R.; Nerurkar, B. M.; Golebiowski, A.; Sundram, H.; Esker, J. L. J. Chem. Soc., Chem. Commun. 1995, 1139.
353. Kitade, Y.; Kozaki, A. Yatome, C. Tetrahedron Lett. 2001, 42, 433.
354. (a) De Clercq, E. Biochem. Pharmacol. 1987, 36, 2567.
355. (b) De Clerq, E. Nucleosides Nucleotides 1998, 17, 625.
356. (c) Wolfe, M. S.; Borchardt, R. T. J. Med. Chem. 1991, 34, 1521.
357. (a) Bitonti, A. J.; Baumann, R. J.; Jarvi, E. T.; McCarthy, J. R.; McCann, P. P. Biochem. Pharmacol. 1990, 40, 601.
358. (b) Henderson, D. M.; Hanson, S.; Allen, T.; Wilson, K.; Coulter-Karis, D. E.; Greenberg, M. L.; Hershfield, M. S.; Ullman, B. Mol. Biochem. Parasitol. 1992, 151, 169.
359. (a) Wolos, J. A.; Frondorf, K. A.; Esser, R. E. J. Immunol. 1993, 151, 526.
360. (b) Wolos, J. A.; Frondorf, K. A.; Babcock, G. F.; Stripp, S. A.; Bowling, T. L. Cell. Immunol. 1993, 149-402.
361. (a) Hasobe, M. J.; McKee, G.; Borcherding, D. R.; Borchardt, R. T. Antimicrob. Agents Chemother. 1987, 31, 1849.
362. (b) Obara, T.; Shuto, S.; Saito, Y.; Snoeck, R.; Andrei, G.; Balzarini, J.; De Clercq, E.; Matsuda, A. J. Med. Chem. 1996, 39, 3847.
363. Seley, K. L.; Schneller, S. W.; De Clercq, E.; Rattendi, D.; Lane, S.; Bacchi, C. J.; Korba, B. Bioorg. Med. Chem. Lett. 1998, 6, 797.
364. Seley, K. L.; Schneller, S. W.; Korba, N. Nucleosides Nucleotides 1997, 16, 2095.
365. Rajappan, V.; Schneller, S. W.; Williams, S. L.; Kern, E. R. Bioorg. Med. Chem. Lett. 2002, 10, 883.
366. Seley, K. L.; Schneller, S. W.; Rattendi, D. Bacchi, C. J. J. Med. Chem. 1997, 40, 622.
367. Nokami, J.; Matsuura, H.; Nakashima, K.; Shibata, S. Chem. Lett. 1994, 1071
368. Saville-Stones, E. A.; Lindell, S. D.; Jennings, N. S.; Head, J. C.; Ford, M. J. J. Chem. Soc., Perkin Trans. 1 1991, 2603.
369. Saville-Stones, E. A.; Turner, R. M.; Lindell, S. D.; Jennings, N. S.; Head, J. C.; Carver, D. S. Tetrahedron 1994, 50, 6695.
370. (a) McKeith, R. A.; McCague, R.; Olivo, H. F.; Palmer, C. F.; Roberts, S. M. J. Chem. Soc., Perkin Trans. 1 1993, 313.
371. (b) Olivo, H. F.; Yu, J. J. Chem. Soc., Perkin Trans. 1 1998, 391.
372. (a) Crimmins, M. T.; King, B. W. J. Org. Chem. 1996, 61, 4192.
373. (b) Crimmins, M. T.; King, B. W.; Zuercher, W. J.; Choy, A. L. J. Org. Chem. 2000, 65, 8499.
374. Burlina, F.; Clivio, P.; Fourrey, J.-L.; Riche, C.; Thomas, M. Tetrahedron Lett. 1994, 35, 8151.
375. Burlina, F.; Favre, A.; Fourrey, J.-L.; Thomas, M. Bioorg. Med. Chem. Lett. 1997, 7, 247.
376. Aggarwal, V. K.; Monteiro, N.; Tarver, G. J.; Lindell, S. D. J. Org. Chem. 1996, 61, 1192.
377. (a) Cabib, E. Antimicrob. Agents Chemother. 1991, 35, 170.
378. (b) Chapman, T.; Kinsman, O.; Houston, J. Antimicrob. Agents Chemother. 1992, 36, 1909.
379. Zhang, D.; Ghosh, A.; Sülling, C.; Miller, M. J. Tetrahedron Lett. 1996, 37, 3799.
380. Mulvihill, M. J.; Miller, M. J. Tetrahedron 1998, 54. 6605.
381. Zhang, D.; Miller, M. J. J. Org. Chem. 1998, 63, 755.
382. (a) Firestein, G.; Boyle, D.; Bullough, D. A.; Gruber, H. E.; Saijadi, F. G.; Montag, A.; Sambol, B.; Mullane, K. M. J. Immunol. 1994, 152, 5853.
383. (b) Williams, M. Nucleosides Nucleotides 1991, 10, 1087.
384. Cowart, M.; Bennett, M. J.; Kerwin, J. F. J. Org. Chem. 1999, 64, 2240.
385. Trost, B. M.; Madsen, R.; Guile, S. D. Tetrahedron Lett. 1997, 38, 1707.
386. Trost, B. M.; Madsen, R.; Guile, S. D.; Elia, A. E. H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1569.
387. Trost, B. M.; Li, L.; Guile, S. D. J. Am. Chem. Soc. 1992, 114, 8745.
388. Trost, B. M.; Madsen, R.; Guile, S. D.; Brown, B. J. Am. Chem. Soc. 2000, 122, 5947.
389. Ito, Y.; Shibata, T.; Arita, M.; Sawai, H.; Ohno, M. J. Am. Chem. Soc. 1981, 103, 6739.
390. (a) Konkel, M. J.; Vince, R. J. Org. Chem. 1996, 61, 6199.
391. (b) Wang, J.; Herdewijn, P. J. Org. Chem. 1999, 64, 7820.
392. (c) Herdewijn, P.; De Clercq, E. Bioorg. Med. Chem. Lett. 2001, 11, 1591.
393. Merlo, V.; Reece, F. J.; Roberts, S. M.; Gregson, M.; Storer, R. J. Chem. Soc., Perkin Trans. 1 1993, 1717.
394. (a) Nokami, J.; Matsuura, H.; Takahashi, H.; Yamashita, M. Synlett. 1994, 491.
395. (b) Kato, K.; Suzuki, H.; Tanaka, H.; Miyasaka, T. Tetrahedron: Asymmetry 1998, 9, 911.
396. Johnson, J. R.; Penning, T. D. J. Am. Chem. Soc. 1986, 108, 5655.
397. (a) Tsuji, J.; Shimizu, I.; Minami, I. Chem. Lett. 1984, 1017.
398. (b) Tsuji, J.; Minami, I.; Shimizu, I. Synthesis 1986, 623.
399. (a) Matsuda, A.; Okajima, H.; Ueda, T. Heterocycles 1989, 29, 25.
400. (b) Matsuda, A.; Okajima, H.; Masuda, A.; Kakefuda, A.; Yoshimura, Y.; Ueda, T. Nucleosides Nucleotides 1992, 11, 197.
401. Czernicki, S.; Ezzitouni, A. J. Org. Chem. 1992, 57, 7325.
402. Crimmins, M. T.; Zuercher, W. J. Org. Lett. 2000, 2, 1065.
403. Ko, O. H.; Hong, J. H. Tetrahedron Lett. 2002, 43, 6399.
404. Hegedus, L. S.; Hervert, K. L.; Matsui, S. J. Org. Chem. 2002, 67, 4076.
405. Hirota, K.; Kitade, Y.; Kanbe, Y.; Isobe, Y.; Maki, Y. Synthesis 1993, 213.
406. Hirota, K.; Kitade, Y.; Kanbe, Y.; Isobe, Y.; Maki, Y. J. Org. Chem. 1992, 57, 5268.
407. (a) De Vos, E.; Esmans, E. L.; Alderweireldt, F. C.; Balzarini, J.; De Clercq, E. J. Heterocycl. Chem. 1993, 30, 1245.
408. (b) Prasad, A. S., B.; Stevenson, T. M.; Citineni, J. R.; Nyzam, V.; Knochel, P. Tetrahedron 1997, 53, 7237.
409. Crouch, G. J.; Eaton, B. E. Nucleosides Nucleotides 1994, 13, 939.
410. Sanpei, K.; Saito, Y.; Imoto, M.; Umezawa, K.; Kato, K. Bioorg. Med. Chem. Lett. 1996, 6, 2487.
411. Nishioka, H.; Sawa, T.; Nakamura, H.; Iinuma, H.; Ikeda, D.; Sawa, R.; Naganawa, H.; Hayashi, C.; Hamada, M.; Takeuchi, T.; Iitaka, Y.; Umezawa, K. J. Nat. Prod. 1991, 54, 1321.
412. (a) Haraguchi, K.; Itoh, Y.; Tanaka, H.; Miyasaka, T. Tetrahedron Lett. 1991, 32, 3391.
413. (b) Haraguchi, K.; Itoh, Y.; Tanaka, H.; Akita, M.; Miyasaka, T. Tetrahedron 1993, 34, 1371.
414. Walkup, R. D.; Mosher, M. D. Tetrahedron 1993, 49, 9285.
415. (a) Solomon, M. S.; Hopkins, P. B. J. Org. Chem. 1993, 58, 2232.
416. (b) Fidanza, J. A.; McLaughlin, L. W. J. Org. Chem. 1992, 57, 2340.
417. Semmelhack, M. F.; Kim, C.; Zhang, N.; Bodurow, C.; Sanner, M.; Dobler, W.; Meier, M. Pure Appl. Chem. 1990, 62, 2035.
418. Harwood, E. A.; Hopkins, P. B.; Sigurdsson, S. T. J. Org. Chem. 2000, 65, 2959.
419. (a) Hori, M.; Ito, E.; Takita, T.; Umezawa, H. J. Antibiot., Ser. A 1964, 17, 96.
420. (b) Koyama, G.; Umezawa, H. J. Antibiot., Ser. A 1965, 18, 175.
421. (a) Levy, D. E.; Tang, C. Chemistry of C-glycosides; Pergamon Press: New York, 1995.
422. (b) Postema, M. H. D. C-Glycoside Synthesis; CRC Press: London, 1995.
423. Ishizuka, M.; Sawa, T.; Koyama, G.; Takench, T.; Umezawa, H. J. Antibiot. 1968, 21, 1.
424. Hidaka, T.; Katayama, K.; Yamashita, K.; Yamashita, T.; Watanabe, K.; Shimasaki, M.; Ohno, M.; Takeuch, T.; Umezawa, H. J. Antibiot. 1980, 33, 303.
425. (a) Rosowsky, A.; Ghoshal, M.; Solan, V. C. Carbohydr. Res. 1988, 176, 47.
426. (b) Buchanan, J. G.; Smith, D.; Wightman, R. H. J. Chem. Soc., Perkin Trans. 1 1986, 1267.
427. (c) Acton, E. M.; Ryan, K. J. J. Org. Chem. 1984, 49, 528.
428. (d) Buchanan, J. G.; Edgar, A. R.; Hutchinson R. J.; Stobie, A.; Wightman, R. H. J. Chem. Soc., Chem. Commun. 1980, 237.
429. (e) Kalvoda, L. Collect. Czech. Chem. Commun. 1978, 43, 1431.
430. (a) Zhang, H.-C.; Daves, G. D. J. Org. Chem. 1992, 57, 4690.
431. (b) Zhang, H.-C.; Brakta, M.; Daves, G. D. Nucleosides Nucleotides 1995, 14, 105.
432. (a) Chen, J. J.; Walker, J. A.; Liu, W.; Wise, D. S.; Townsend, L. B. Tetrahedron Lett. 1995, 36, 8363.
433. (b) Gundmundsson, K. S.; Drach, J. C.; Townsend, L. B. Tetrahedron Lett. 1996, 37, 6275.
434. (a) Chida, N.; Susuki, T.; Tanaka, S.; Yamada, I. Tetrahedron Lett. 1999, 40, 2573.
435. Susuki, T.; Tanaka, S.; Yamada, I.; Koashi, Y.; Yamada, K.; Chida, N. Org. Lett. 2000, 2, 1137.
436. Wolfe, J. P.; Buchwald, S. L. J. Am. Chem. Soc. 1997, 119, 6054.
437. Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268.
438. Reddy, N. P.; Tanaka, M. Tetrahedron Lett. 1997, 38, 4807.
439. (a) Abbas, S.; Bertram, R. D.; Hayes, C. J. Org. Lett. 2001, 3, 3365.
440. (b) Abbas, S.; Hayes, C. J. Tetrahedron Lett. 2000, 41, 4513.
441. (c) Abbas, S.; Hayes, C. J. Synlett 1999, 1124.
442. Sessler, J. L.; Wang, R. J. Am. Chem. Soc. 1996, 118, 9808.
443. Sessler, J. L.; Wang, R. J. Org. Chem. 1998, 63, 4079.
444. Hocek, M.; Votruba, I. Bioorg. Med. Chem. Lett. 2002, 12, 1055.
445. (a) Gunji, H.; Vasella, A. Helv. Chem. Acta 2000, 83, 2975.
446. (b) Gunji, H.; Vasella, A. Helv. Chem. Acta 2000, 83, 3229.
447. Gunji, H.; Vasella, A. Helv. Chim. Acta 2000, 83, 1331.
448. During the revision of this paper, several articles on palladium-assisted routes to nucleosides were published: (a) Lobaton, E.; Rodriguez-Barrios, F.; Gago, F.; Perez-Perez, M.-J.; De Clercq, E.; Balzarini, J.; Camarasa, M.-J.; Velasquez, S. J. Med. Chem. 2002, 45. 3934.
449. (b) Suzuki, T.; Suzuki, S. T.; Yamada, I.; Koashi, Y.; Yamada, K.; Chida, N. J. Org. Chem. 2002, 67, 2874.
450. (c) Velcicky, J.; Lex, J.; Schmalz, H.-G. Org. Lett. 2002, 4, 565.