Furan and Its Derivatives

Heterocycles in Natural Product Synthesis

Volumn , Issue , 2011, Pages 97-152

  Boto, Alicia ^a   Alvarez, Laura ^b  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

^b CENTRO DE INVESTIGACIONES QUÍMICAS   (Mexico)

Author keywords

Common ring heterocycles; Furan; Heterocycles; Natural products; Synthesis

Indexed keywords

EID: 84859147523     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527634880.ch4     Document Type: Chapter

References (463)

1. Furan in natural products, acetogenins, macrolides and other polyether derivatives: Nicolaou, K.C. (2009) J. Org. Chem., 74, 951-972
2. Paterson, I., and Dalby, S.M. (2009) Nat. Prod. Rep., 26, 865-873
3. Nicolaou, K.C., Frederick, M.O. and Aversa, R.J. (2008) Angew. Chem. Int. Ed., 47, 7182-7225
4. Maezaki, N., Kojima, N. and Tanaka, T. (2006) Synlett, 993-1003
5. Hale, K.J., Hummersone, M.G., Manaviazar, S. and Frigerio, M. (2002) Nat. Prod. Rep., 19, 413-453
6. Faul, M.M. and Huff, B.E. (2000) Chem. Rev., 100, 2407-2473.
7. Furan in terpenes and steroids: Gaich, T., Weinstabl, H. and Mulzer, J. (2009) Synlett, 1357-1366
8. Yue, J.M., Liao, S.G. and Chen, H.D. (2009) Chem. Rev., 109, 1092-1140
9. Prisinzano, T.E. and Rothman, R.B. (2008) Chem. Rev., 108, 1732-1743
10. González, M.A. (2008) Tetrahedron, 64, 445-467
11. Fraga, B.M. (2008) Nat. Prod. Rep., 25, 1180-1209
12. Busch, T. and Kirschning, A. (2008) Nat. Prod. Rep., 25, 318-341
13. Keyzers, R.A., Northcote, P.T. and Davies-Coleman, M.T. (2006) Nat. Prod. Rep., 23, 321-334
14. Liu, Y., Zhang, S. and Abreu, P.J.M. (2006) Nat. Prod. Rep., 23, 630-651
15. Maifeld, S.V. and Lee, D. (2006) Synlett, 1623-1644
16. Hanson, J.R. (2006) Nat. Prod. Rep., 23, 875-885
17. Wipf, P. and Halter, R.J. (2005) Org. Biomol. Chem., 3, 2053-2061
18. Connolly, J.D. and Hill, R.A. (2005) Nat. Prod. Rep., 22, 230-248
19. Maurya, R. and Yadav, P.P. (2005) Nat. Prod. Rep., 22, 400-424
20. Steyn, P.S. and van Heerden, F.R. (1998) Nat. Prod. Rep., 15, 397-413.
21. Furan in Lignans: Saleem, M., Kim, H.J., Ali, M.S. and Lee, Y.S. (2005) Nat. Prod. Rep., 22, 696-716.
22. Tetronic acids: Schobert, R. and Schlenk, A. (2008) Bioorg. Med. Chem., 16, 4203-4221.
23. Cembranes, cembranolides: Roethle, P.A. and Trauner, D. (2008) Nat. Prod. Rep., 25, 298-317
24. Tius, M.A. (1988) Chem. Rev., 88, 719-732.
25. Furan in alkaloids and as precursor of alkaloids: Weinreb, S.M. (2009) Nat. Prod. Rep., 26, 758-775
26. Jin, Z. (2009) Nat. Prod. Rep., 26, 363-381
27. Michael, J.P. (2008) Nat. Prod. Rep., 25, 139-165
28. Jin, Z. (2007) Nat. Prod. Rep., 24, 886-905
29. Michael, J.P. (2005) Nat. Prod. Rep., 22, 603-626
30. Pilli, R.A. and Ferreira de Oliveira, M.C. (2000) Nat. Prod. Rep., 17, 117-128
31. Casiraghi, C., Zanardi, F., Rassu, G. and Spanu, P. (1995) Chem. Rev., 95, 1677-1716.
32. Furan in other natural products: Nandy, J.P., Prakesch, M., Khadem, S., Reddy, P.T., Sharma, U. and Arya, P. (2009) Chem. Rev., 109, 1999-2060
33. Bräse, S., Encinas, A., Keck, J. and Nising, C.F. (2009) Chem. Rev., 109, 3903-3990
34. Blunt, J.W., Copp, B.R., Hu, W.P., Munro, M.H.G., Northcote, P.T. and Prinsep, M.R. (2009) Nat. Prod. Rep., 26, 170-245
35. Lachia, M. and Moody, C.J. (2008) Nat. Prod. Rep., 25, 227-254
36. Sperry, J., Bachu, P. and Brimble, M.A. (2008) Nat. Prod. Rep., 25, 376-400
37. Cordier, C., Morton, D., Murrison, S., Nelson, A. and O'Leary -Steele, C. (2008) Nat. Prod. Rep., 25, 719-737
38. Veitch, N.C. and Grayer, R.J. (2008) Nat. Prod. Rep., 25, 555-612
39. Skoropeta, D. (2008) Nat. Prod. Rep., 25, 1131-1166
40. Shoji, M. and Hayashi, Y. (2007) Eur. J. Org. Chem., 3783-3800
41. Blunt, J.W., Copp, B.R., Munro, M.H.G., Northcote, P.T. and Prinsep, M.R. (2003) Nat. Prod. Rep., 20, 1-48
42. Faulkner, D.J. (2000) Nat. Prod. Rep., 17, 7-56
43. Nicolaou, K.C., Vourloumis, D., Winssinger, N. and Baran, P.S. (2000) Angew. Chem. Int. Ed., 39, 44-122
44. Mehta, G. and Singh, V.K. (1999) Chem. Rev., 99, 881-930
45. Cereghetti, D.M. and Carreira, E.M. (2006) Synthesis, 914-942.
46. Lipshutz, B.H. (1986) Chem. Rev., 86, 795-819
47. Rodrigo, R. (1988) Tetrahedron, 44, 2093-2135.
48. Synthesis of furan derivatives and their applications: Brichacek, M. and Njardarson, J.T. (2009) Org. Biomol. Chem., 7, 1761-1770
49. Wolfe, J.P. and Hay, M.B. (2007) Tetrahedron, 63, 261-290
50. Bellur, E., Feist, H. and Langer, P. (2007) Tetrahedron, 63, 10865-10888
51. Kirsch, S.F. (2006) Org. Biomol. Chem., 4, 2076-2080
52. Zografos, A.L. and Georgiadis, D. (2006) Synthesis, 3157-3188
53. Brown, R.C.D. (2005) Angew. Chem. Int. Ed., 44, 850-852
54. Keay, B.A. (1999) Chem. Soc. Rev., 28, 209-215
55. Wong, H.N.C. (1996) Pure Appl. Chem., 68, 335-344
56. Hou, X.L., Cheung, H.Y., Hon, T.Y., Kwan, P.L., Lo, T.H., Tong, S.Y. and Wong, H.C.N. (1998) Tetrahedron, 54, 1955-2020.
57. Angelmarin (1): Jiang, H. and Hamada, Y. (2009) Org. Biomol. Chem., 7, 4173-4176
58. Magolan, J. and Coster, M.J. (2009) J. Org. Chem, 74, 5083-5086.
59. 6-C-β-manno pyranosylapigenin (2): Veitch, N.C. and Grayer, R.J. (2008) Nat. Prod. Rep., 25, 555-611
60. Nakatsuka, T., Tomimori, Y., Fukuda, Y. and Nukaya, H. (2004) Bioorg. Med. Chem. Lett., 14, 3201-3203
61. Furuta, T., Kimura, T., Kondo, S., Mihara, H., Wakimoto, T., Nukaya, H., Tsuji, K. and Tanaka, K. (2004) Tetrahedron, 60, 9375-9379.
62. Asiminocin (3): Marshall, J.A., Piettre, A., Paige, M.A. and Valeriote, F. (2003) J. Org. Chem., 68, 1771-1779
63. Elliott, M.C. and Williams, E. (2001) J. Chem. Soc. Perkin Trans. 1, 2303-2340
64. Elliott, M.C. (2000) J. Chem. Soc. Perkin Trans. 1, 1291-1318
65. McLaughlin, J.L. (2008) J. Nat. Prod., 71, 1311-1321.
66. Bhimamycin B (4): Uno, H., Murakami, S., Fujimoto, A., Yamaoka, Y. (2005) Tetrahedron Lett., 46, 3997-4000.
67. Cantharidin (5): Deng, L., Shen, L., Zhang, J., Yang, B., He, Q. and Hu, Y. (2007) Can. J. Chem., 85, 938-944
68. For analogs, see: Baba, Y., Hirukawa, N. and Sodeoka, M. (2005) Bioorg. Med. Chem., 13, 5164-5170
69. Palasonin: Dauben, W.G., Lam, J.Y.L. and Guo, Z.R. (1996) J. Org. Chem., 61, 4816-4819.
70. Cephalostatin (6): Lee, S., LaCour, T.G. and Fuchs, P.L. (2009) Chem. Rev., 109, 2275-2314.
71. CP-263,114 (7): Splegel, D.A., Njardarson, J.T., McDonald, I.M. and Wood, J.L. (2003) Chem. Rev., 103, 2691-2727.
72. Eleutherobin (8): Castoldi, D., Caggiano, L., Panigada, L., Sharon, O., Costa, A.M. and Gennari, C. (2005) Chemistry, 12, 51-62
73. Sperry, J.B., Constanzo, J.R., Jasinski, J., Butcher, R.J. and Wright, D.L. (2005) Tetrahedron Lett., 46, 2789-2793
74. Diederichsen, U. (2003) Org. Synth. Highlights, 317-325
75. Chen, X.T., Bhattacharya, S.K., Zhou, B., Gutteridge, C.E., Pettus, T.R.R. and Danishefsky, S.J. (1999) J. Am. Chem. Soc., 121, 6563-6579.
76. Furoscrobiculin (9): Seki, M., Sakamoto, T., Suemune, H. and Kanematsu, K. (1997) J. Chem. Soc. Perkin Trans. 1, 1707-1714.
77. Ginkgolide B1 (10): Gosh, A.K. (2009) J. Med. Chem., 52, 2163-2176
78. Vogensen, S.B., Stromgaard, K., Shindou, H., Jaracz, S., Suehiro, M., Ishii, S., Shimizu, T. and Nakanishi, K. (2003) J. Med. Chem., 46, 601-608
79. Crimmins, M.T., Pace, J.M., Nantermet, P.G., Kim-Meade, A.S., Thomas, J.B., Watterson, S.H. and Wagman, A.S. (2000) J. Am. Chem. Soc., 122, 8453-8463
80. Corey, E.J., Kang, M., Desai, M.C., Ghosh, A.K. and Houpis, I.N. (1988) J. Am. Chem. Soc., 110, 649-651.
81. Goniofufurone (11): Prasad, K.R. and Gholap, S.I. (2008) J. Org. Chem., 73, 2-11.
82. Medermycin (12): Brimble, M.A. and Brenstrum, T.J. (2001) J. Chem. Soc. Perkin Trans. 1, 1624-1634
83. Brimble, M.A. (2000) Pure Appl. Chem., 72, 1635-1639
84. For related griseusin, see: Brimble, M.A., Nairn, M.R. and Park, J.S.O. (1999) Org. Lett., 1, 1459-1462.
85. Moracin O (13): Kaur, N., Xia, Y., Dat, N.T., Gajulapati, K., Choi, Y., Hong, Y.S., Lee, J.J. and Lee, K. (2009) Chem. Commun., 1879-1881.
86. Morphine (14): Tanimoto, H., Saito, R. and Chida, N. (2008) Tetrahedron Lett., 49, 358-362
87. Omori, A.T., Finn, K.J., Leisch, H., Carroll, R.J. and Hudlicky, T. (2007) Synlett, 2859-2862
88. Uchida, K., Yokoshima, S., Kan, T. and Fukuyama, T. (2006) Org. Lett., 8, 5311-5313
89. Parker, K.A. and Fokas, D. (2006) J. Org. Chem., 71, 449-455
90. Trost, B.M. and Toste, F.D. (2005) J. Am. Chem. Soc., 127, 14785-14803
91. Novak, B.H., Hudlicky, T., Reed, J.W., Mulzer, J. and Trauner, D. (2000) Curr. Org. Chem., 4, 343-362.
92. Norhalichondrin B (15): Phillips, A.J., Jackson, K.L. and Henderson, J.A. (2009) Chem. Rev., 109, 3044-3079
93. Jackson, K.L., Henderson, J.A., Motoyoshi, H. and Phillips, A.J. (2009) Angew. Chem. Int. Ed., 48, 2346-2350.
94. Pallescensin A (16): Foot, J.S., Phillis, A.T. and Sharp, P.P. (2006) Tetrahedron Lett., 47, 6817-6820.
95. Pamamycin (17): Wang, Y., Bernsmann, H., Gruner, M. and Metz, P. (2001) Tetrahedron Lett., 42, 7801-7804
96. Metz, P. (2005) Top. Curr. Chem., 244 (Natural Product Synthesis II), 215-249
97. Kang, E.J. and Lee, E. (2005) Chem. Rev., 105, 4348-4378.
98. Panacene (18): Sabot, C., Berard, D. and Canesi, S. (2008) Org. Lett., 10, 4629-4632
99. Boukouvalas, J., Pouliot, M., Robichaud, J., McNeil, S. and Snieckus, V. (2006) Org. Lett., 8, 3597-3599.
100. Podophyllotoxin (19): Wu, Y., Zhao, J., Chen, J., Pan, C., Li, L. and Zhang, H. (2009) Org. Lett., 11, 597-600
101. Wu, Y., Zhang, H., Hao, Y., Zao, J., Chen, J. and Li, L. (2007) Org. Lett., 9, 1199-1202
102. Reynolds, A.J., Scott, A.J., Turner, C.I. and Sherburn, M.S. (2003) J. Am. Chem. Soc., 125, 12108-12109
103. Berkowitz, D.B., Choi, S. and Maeng, J.H. (2000) J. Org. Chem., 65, 847-860
104. For epi-podophyllotoxin, see: Engelhardt, U., Sarkar, A., Linker, T. (2003) Angew. Chem. Int. Ed., 42, 2887-2889
105. Ward, R.S. (1999) Nat. Prod. Rep., 161, 75-96
106. Ward, R.S. (1992) Synthesis, 719-730.
107. Polyoxin (20): Luo, Y.C., Zhang, H.H., Liu, Y.Z., Cheng, R.L. and Xu, P.F. (2009) Tetrahedron Asymmetry, 20, 1174-1180
108. Dondoni, A., Franco, S., Junquera, F., Merchan, F.L., Merino, P. and Tejero, T. (1997) J. Org. Chem., 62, 5497-5507
109. For related nikkomycin, see: Hayashi, Y., Urushima, T., Shin, M. and Shoji, M. (2005) Tetrahedron, 61, 11393-11404.
110. Proximicins (21): Schneider, K., Keller, S., Wolter, F.E., Röglin, L., Beil, W., Seitz, O., Nicholson, G., Bruntner, C., Riedlinger, J., Fiedler, H.P. and Süssmuth, R.D. (2008) Angew. Chem. Int. Ed., 47, 3258-3261
111. Wolter, F.E., Molinari, L., Socher, E.R., Schneider, K., Nicholson, G., Beil, W., Seitz, O. and Süssmuth, R.D. (2009) Bioorg. Med. Chem. Lett., 19, 3811-3815.
112. Rhizonin A (22): Nakatsuka, H., Shimokawa, K., Miwa, R., Yamada, K. and Uemura, D. (2009) Tetrahedron Lett., 50, 186-188.
113. Salvinorin (23): Simpson, D.S., Katavic, P.L., Lozama, A., Harding, W.W., Parrish, D., Deschamps, J.R., Dersch, C.M., Partilla, J.S., Rothman, R.B., Navarro, H. and Prisinzano, T.E. (2007) J. Med. Chem., 50, 3596-3603.
114. Securinine (24): Weinreb, S.M. (2009) Nat. Prod. Rep., 26, 758-775
115. Dhudshia, B., Cooper, B.F.T., MacDonald, C.L.B. and Thadani, A.N. (2009) Chem. Commun., 463-465
116. Leduc, A.B. and Kerr, M.A. (2008) Angew. Chem. Int. Ed., 47, 7945-7948
117. Carson, C.A. and Kerr, M.A. (2006) Angew. Chem. Int. Ed., 45, 6560-6563
118. Honda, T., Namiki, H., Watanabe, N. and Mizutani, H. (2004) Tetrahedron Lett., 45, 5211-5213
119. Alibes, R., Ballbe, M., Busque, F., De March, P., Elias, L., Figueredo, M. and Font, J. (2004) Org. Lett., 6, 1813-1816 and references cited therein.
120. Spirastrellolide A (25): Paterson, I., Anderson, E.A., Dalby, S.M., Lim, J.H., Genovino, J., Maltas, P. and Moessner, C. (2008) Angew. Chem. Int. Ed., 47, 3016-3020
121. Paterson, I. Anderson, E.A., Dalby, S.M., Lim, J.H., Genovino, J., Maltas, P. and Moessner, C. (2008) Angew. Chem. Int. Ed., 47, 3021-3025
122. Paterson, I. and Dalby, S.M. (2009) Nat. Prod. Rep., 26, 865-873.
123. Spirolide (26): Meilert, K. and Brimble, M.A. (2006) Org. Biomol. Chem., 4, 2184-2192
124. Ishihara, J., Ishizaka, T., Suzuki, T. and Hatakeyama, S. (2004) Tetrahedron Lett., 45, 7855-7858.
125. Uprolide D (27): Marshall, J.A. and Hann, R. (2008) J. Org. Chem., 73, 6753-6757
126. For the structurally related, neurotoxic pukalide, see: Donohoe, T.J., Ironmonger, A. and Kershaw, N.M. (2008) Angew. Chem. Int. Ed., 47, 7314-7316.
127. Xanthohumol (28): Wang, W.S., Zhou, Y.W., Ye, Y.H. and Li, M.L. (2004) Chin. Chem. Lett., 15, 1195-1196.
128. XH-14 (29): Kao, C.L. and Chern, J.W. (2002) J. Org. Chem., 67, 6772-6787
129. Lütjens, H. and Scammells, J. (1998) Tetrahedron Lett., 39, 6581-6584.
130. Yangambin (30): Mori, N., Watanabe, H. and Kitahara, T. (2006) Synthesis, 400-404.
131. Zaragozic acid (31): Nakamura, S., Sato, H., Hirata, Y., Watanabe, N. and Hashimoto, S. (2005) Tetrahedron, 61, 11078-11106
132. Armstrong, A. and Blench, T.J. (2002) Tetrahedron, 58, 9321-9349
133. Schlessinger, R.H., Wu, X.H. and Pettus, T.R.R. (1995) Synlett, 536-538.
134. Preparation of furans using radical reactions: Majumdar, K.C., Basu, P.K. and Mukhopadhyay, P.P. (2007) Tetrahedron, 63, 793-826
135. Majumdar, K.C., Basu, P.K. and Mukhopadhyay, P.P. (2005) Tetrahedron, 61, 10603-10642
136. Majumdar, K.C., Basu, P.K. and Mukhopadhyay, P.P. (2004) Tetrahedron, 60, 6239-6279
137. Procter, D.J., Edmons, D.J. and Johnston, D. (2004) Chem. Rev., 104, 3371-3403
138. Hartung, J. (2001) Eur. J. Org. Chem., 619-632
139. Hartung, J., Gottwald, T. and Spehar, K. (2002) Synthesis, 1469-1498.
140. Preparation of furans using epoxide ring opening: Marshall, J.A. and Hann, R.K. (2008) J. Org. Chem., 73, 6753-6757
141. Berber, H., Delaye, P.O. and Mirand, C. (2008) Synlett, 94-96
142. Gupta, S., Rajagopalan, M., Alhamadsheh, M.M., Tillekeratne, L.M.V. and Hudson, R.A. (2007) Synthesis, 3512-3518
143. Curran, D.P., Zhang, Q., Richard, C., Lu, H., Gudipati, V. and Wilcox, C.S. (2006) J. Am. Chem. Soc., 128, 9561-9573
144. Halim, R., Brimble, M.A. and Merten, J. (2005) Org. Lett., 7, 2659-2662.
145. Haloeterification and haloesterification: Carley, S. and Brimble, M.A. (2009) Org. Lett., 11, 563-566
146. Wang, C., Zhang, H., Liu, J., Shao, Z., Ji, Y. and Li, L. (2006) Synlett, 1051-1054
147. Gu, Y. and Snider, B.B. (2003) Org. Lett., 5, 4385-4388
148. Kinoshita, A. and Mori, M. (1996) J. Org. Chem., 61, 8356-8357.
149. Reduction and oxidations: Zhou, Y.G. (2007) Acc. Chem. Res., 40, 1357-1366
150. Vassilikogiannakis, G., Montagnon, T. and Tofi, M. (2008) Acc. Chem. Res., 41, 1001-1010
151. Yoshida, J.-I., Kataoka, K., Horcajada, R. and Nagaki, A. (2008) Chem. Rev., 108, 2265-2299
152. Hudlicky, T., Entwistle, D.A., Pitzer, K.K. and Thorpe, A.J. (1996) Chem. Rev., 96, 1195-1220
153. Holder, N.L. (1982) Chem. Rev., 82, 267-332.
154. Oxycarbenium ions and furan-derived nucleophiles (such as TMSOF): Harmata, M. and Rashatasakhon, P. (2003) Tetrahedron, 59, 2371-2395
155. Martin, S.F. (2002) Acc. Chem. Res., 35, 895-904
156. Rassu, G., Zanardi, F., Battistini, L. and Casiraghi, G. (2000) Chem. Soc. Rev., 29, 109-118.
157. Diels-Alder reactions: Clarke, P.A., Reeder, A.T. and Winn, J. (2009) Synthesis, 691-709
158. Reymond, S. and Cossy, J. (2008) Chem. Rev., 108, 5359-5406
159. Takao, K.I., Munakata, R. and Tadano, K.I. (2005) Chem. Rev., 105, 4779-4807
160. Nicolaou, K.C., Snyder, S.A., Montagnon, T. and Vassilikogiannakis, G. (2002) Angew. Chem. Int. Ed., 41, 1668-1698
161. Kappe, C.O., Murphree, S.S. and Padwa, A. (1997) Tetrahedron, 53, 14179-14233
162. Winkler, J.D. (1996) Chem. Rev., 96, 167-176
163. Brieger, G. and Bennet, J.N. (1980) Chem. Rev., 80, 63-97
164. See also: Jacobi, P.A. and Lee, K. (1997) J. Am. Chem. Soc., 119, 3409-3410 and references cited therein.
165. Dipolar cycloadditions: Pellisier, H. (2007) Tetrahedron, 63, 3235-3285
166. Nair, V. and Suja, T.D. (2007) Tetrahedron, 63, 12247-12275
167. Padwa, A. and Weingarten, M.D. (1996) Chem. Rev., 96, 223-269
168. Padwa, A. (1991) Acc. Chem. Res., 24, 22-28
169. For other cycloaddition processes, see: Liao, C.C. and Peddinti, R.K. (2002) Acc. Chem. Res., 35, 856-866
170. Harmata, M. (2001) Acc. Chem. Res., 34, 595-605.
171. Nicolaou, K.C., Bulger, P.G. and Sarlah, D. (2005) Angew. Chem. Int. Ed., 44, 4490-4527
172. Grubbs, R.H. (ed.) (2003) Handbook of Metathesis, Wiley-VCH Verlag GmbH, Weinheim, Germany, ISBN: 3-527-30616-1.
173. Carbenes: Dotz, K.H. and Stendel, J. (2009) Chem. Rev., 109, 3227-3274
174. Warkentin, J. (2009) Acc. Chem. Res., 42, 205-212
175. Cheng, Y. and Meth-Cohn, O. (2004) Chem. Rev., 104, 2507-2503
176. Müller, P. (2004) Acc. Chem. Res., 37, 243-251
177. Reissig, H.U. and Zimmer, R. (2003) Chem. Rev., 103, 1151-1196
178. Davies, H.M.L. and Beckwith, R.E.J. (2003) Chem Rev., 103, 2861-2903
179. Sierra, M.A. (2000) Chem. Rev., 100, 3591-3637
180. Doyle, M.P. and Forbes, D.C. (1998) Chem. Rev., 98, 911-935
181. Ye, T. and McKervey, M.A. (1994) Chem. Rev., 94, 1091-1160.
182. Other metal-catalyzed furan synthesis: Alvarez-Corral, M., Muñoz-Dorado, M. and Rodriguez-Garcia, I. (2008) Chem. Rev., 108, 3174-3198
183. Yamamoto, Y. and Patil, N.T. (2008) Chem. Rev., 108, 3395-3442
184. Hashmi, A.S.K. (2007) Chem. Rev., 107, 3180-3211
185. Ma, S. (2005) Chem. Rev., 105, 2829-2871
186. Schröter, S., Stock, C. and Bach, T. (2005) Tetrahedron, 61, 2245-2267
187. Zeni, G. and Larock, R.C. (2004) Chem. Rev., 104, 2285-2309
188. Trost, B.M. and Crawley, M.L. (2003) Chem. Rev., 103, 2921-2943
189. Yet, L. (2000) Chem. Rev., 100, 2963-3007.
190. For recent examples of metal-catalyzed furan synthesis, see: Brasholz, M. and Reissig, H.U. (2009) Eur. J. Org. Chem., 3595-3604
191. Istrate, F.M. and Gagosz, F.L. (2008) J. Org. Chem., 73, 730-733
192. Marshall, J.A. and Van Devender, E.A. (2001) J. Org. Chem., 66, 8037-8041
193. Hiroya, K., Suzuki, N., Yasuhara, A., Egawa, Y., Kasano, A. and Sakamoto, T. (2000) J. Chem. Soc. Perkin Trans. 1, 4339-4346
194. Lutjens, H. and Scammells, P.J. (1998) Tetrahedron Lett., 39, 6581-6584
195. Marshall, J.A. and Sehan, C.A. (1997) J. Org. Chem., 62, 4313-4320.
196. Furans using biomimetic reactions, multicomponent processes and cascade reactions: Touré, B.B. and Hall, D.G. (2009) Chem. Rev., 109, 4439-4486
197. Bulger, P.G., Bagal, S.K. and Marquez, R. (2008) Nat. Prod. Rep., 25, 254-297
198. Padwa, A. and Bur, S.K. (2007) Tetrahedron, 63, 5341-5378
199. Nicolaou, K.C., Edmons, D.J. and Bulger, P.G. (2006) Angew. Chem. Int. Ed., 45, 7134-7186
200. Parsons, P.J., Penkett, C.S. and Shell, A.J. (1996) Chem. Rev., 96, 195-206
201. Parsons, P.J., Penkett, C.S. and Shell, A.J. (1996) Chem. Rev., 96, 195-206.
202. Ketalization, furans from ketals: Boto, A., Hernández, D. and Hernández, R. (2007) Org. Lett., 9, 1721-1724
203. Jung, M.E. and Min, S.J. (2004) Tetrahedron Lett., 45, 6753-6755
204. Fenlon, T.W., Schwaebisch, D., Mayweg, A.V.W., Lee, V., Adlington, R.M. and Baldwin, J.E. (2007) Synlett, 2679-2682
205. Gennari, C., Castoldi, D. and Sharon, O. (2007) Pure Appl. Chem., 79, 173-180
206. For some synthesis of furans from sugars, see: Mereyala, H.B., Gadikota, R.R. and Krishnan, R. (1997) J. Chem. Soc. Perkin Trans. 1, 3567-3571
207. Dixon, D.J., Ley, S.V., Gracza, T. and Szolcsanyi, P. (1999) J. Chem. Soc. Perkin Trans. 1, 839-841
208. Yoon, S.H., Moon, H.S., Hwang, S.K., Choi, S. and Kang, S.K. (1998) Bioorg. Med. Chem., 6, 1043-1049
209. Mereyala, H.B., Gadikota, R.R., Joe, M., Arora, S.K., Dastidar, S.G. and Agarwal, S. (1999) Bioorg. Med. Chem., 7, 2095-2103.
210. Rearrangements: Bur, S.K. and Padwa, A. (2004) Chem. Rev., 104, 2401-2432
211. Tsubuki, M., Ohinata, A., Tanaka, T., Takahashi, K. and Honda, T. (2005) Tetrahedron, 61, 1095-1100
212. Caruana, P.A. and Frontier, A.J. (2004) Tetrahedron, 60, 10921-10926.
213. For some synthesis of lactones and their reactions, see: Prasad, K.R. and Gholap, S.L. (2008) J. Org. Chem., 73, 2-11
214. Huang, Y. and Pettus, T.R.R. (2008) Synlett, 1353-1356
215. Lee, C.L., Lin, C.F., Lin, W.R., Wang, K.S., Chang, Y., Lin, S.R., Wu, Y.C. and Wu, M.J. (2005) Bioorg. Med. Chem., 13, 5864-5872
216. Krohn, K., Riaz, M. and Flörke, U. (2004) Eur. J. Org. Chem., 1261-1270.
217. For the preparation of benzofuran and isobenzofuran rings and their reactivity, see: McAllister, G.D., Hartley, R.C., Dawson, M.J. and Knaggs, A.R. (1998) J. Chem. Soc. Perkin Trans. 1, 3453-3457
218. Traulsen, T. and Friedrichsen, W. (2000) J. Chem. Soc. Perkin Trans. 1, 1387-1398
219. Uno, H., Murakami, S., Fujimoto, A. and Yamaoka, Y. (2005) Tetrahedron Lett., 46, 3997-4000
220. Dixit, M., Sharon, A., Maulik, P.R. and Goel, A. (2006) Synlett, 1497-1502
221. Slamet, R. and Wege, D. (2007) Tetrahedron, 63, 12621-12628
222. Yue, D., Yao, T. and Larock, R.C. (2005) J. Org. Chem., 70, 10292-10296.
223. Metallation: Chinchilla, R., Nájera, C. and Yus, M. (2005) Tetrahedron, 61, 3139-3176
224. Chinchilla, R., Nájera, C. and Yus, M. (2004) Chem. Rev., 104, 2667-2722.
225. Lithiation: Marcos, I.S., Escola, M.A., Moro, R.F., Basabe, P., Diez, D., Sanz, F., Mollinedo, F., de la Iglesia-Vicente, J., Sierra, B.G. and Urones, J.G. (2007) Bioorg. Med. Chem., 15, 5719-5737
226. Xu, P.F., Luo, Y.C. and Zhang, H.H. (2009) Synlett, 833-837
227. Smitt, O. and Högberg, H. (2002) Synlett, 1273-1276
228. See also: Nakatsuka, H., Shimokawa, K., Miwa, R., Yamada, K. and Uemura, D. (2009) Tetrahedron Lett., 50, 186-188
229. Gogoi, S. and Argade, N.P. (2008) Synthesis, 1455-1459
230. Bruy è re, H., Dos Reis, C., Samaritani, S., Ballereau, S. and Royer, J. (2006) Synthesis, 1673-1681
231. Oh, S., Jeong, I.H., Shin, W.S. and Lee, S. (2003) Bioorg. Med. Chem. Lett., 13, 2009-2012
232. Marshall, J.A., Bartley, G.S. and Wallace, E.M. (1996) J. Org. Chem., 61, 5729-5735
233. Shen, C.C., Chou, S.C., Chou, C.J. and Ho, L.K. (1996) Tetrahedron Asymmetry, 7, 3141-3146.
234. Stannylated derivatives: Roethle, P.A. and Trauner, D. (2006) Org. Lett., 8, 345-347
235. Tan, Q. and Danishefsky, S.J. (2000) Angew. Chem. Int. Ed., 39, 4509-4511
236. Meng, D.F., Tan, Q. and Danishefsky, S.J. (1999) Angew. Chem. Int. Ed., 38, 3197-3201
237. Meng, D.F. and Danishefsky, S.J. (1999) Angew. Chem. Int. Ed., 38, 1485-1488
238. Clark, J.S., Northall, J.M., Marlin, F., Nay, B., Wilson, C., Blake, A.J. and Waring, M.J. (2008) Org. Biomol. Chem., 6, 4012-4025
239. Cases, M., González -López de Turiso, F. and Pattenden, G. (2001) Synlett, 1869-1872
240. Pattenden, G. and Sinclair, D.J. (2002) J. Organomet. Chem., 653, 261-268
241. Paterson, I., Brown, R.E. and Urch, C. (1999) Tetrahedron Lett., 40, 5807-5810
242. Yu, P., Yang, Y., Zhang, Z.Y., Mak, T.C.W. and Wong, H.N.C. (1997) J. Org. Chem., 62, 6359-6366
243. Paterson, I., Brown, R.E. and Urch, C. (1999) Tetrahedron Lett., 40, 5807-5810.
244. Titanium reagents: Sibi, M.P. and He, L. (2004) Org. Lett., 6, 1749-1752.
245. Furyl zincs: Donohoe, T.J., Ironmonger, A. and Kershaw, N.M. (2008) Angew. Chem. Int. Ed., 47, 7314-7316
246. Mukaiyama, T., Suzuki, K., Yamada, T. and Tabusa, F. (1990) Tetrahedron, 46, 265-276.
247. Chromium derivatives: Chen, X.T., Bhattacharya, S.K., Zhou, B., Gutteridge, C.E., Pettus, T.R.R. and Danishefsky, S.J. (1999) J. Am. Chem. Soc., 121, 6563-6579.
248. Silyl derivatives: Chen, W., Wu, H., Bernard, D., Metcalf, M.D., Deschamps, J.R., Flippen-Anderson, J.L., MacKerell, A.D., Jr. and Coop, A. (2003) J. Org. Chem., 68, 1929-1932
249. Tan, Z. and Negishi, E.-I. (2006) Org. Lett., 8, 2783-2785.
250. Seleno derivatives: Brecht-Forster, A., Fitremann, J. and Renaud, P. (2002) Helv. Chim. Acta, 85, 3965-3974.
251. Boranes, boronates, boronic acids: Yick, C.Y., Tsang, T.K. and Wong, H.N.C. (2003) Tetrahedron, 59, 325-333.
252. Reductions: Garçon, S., Vassiliou, S., Cavicchioli, M., Hartmann, B., Monteiro, N. and Balme, G. (2001) J. Org. Chem., 66, 4069-4073
253. Donohoe, T.J., Guillermin, J.B., Frampton, C. and Walter, D.S. (2000) Chem. Commun., 465-466.
254. Achmatowicz to lactones: Henderson, J.A., Jackson, K.L. and Phillips, A.J. (2007) Org. Lett., 9, 5299-5302
255. Guo, H. and O'Doherty, G.A. (2008) J. Org. Chem., 73, 5211-5220
256. Shults, E.E., Velder, J., Schmalz, H.G., Chernov, S.V., Rubalova, T.V., Gatilov, Y.V., Henze, G., Tolstikov, G.A. and Prokop, A. (2006) Bioorg. Med. Chem. Lett., 16, 4228-4232
257. Brasholz, M. and Reissig, H.U. (2007) Synlett, 1294-1298
258. Abrams, J.N., Babu, R.S., Guo, H., Le, D., Le, J., Osbourn, J.M. and O'Doherty, G.A. (2008) J. Org. Chem., 73, 1935-1940
259. Fürstner, A. and Nagano, T. (2007) J. Am. Chem. Soc., 129, 1906-1907
260. Nicolaou, K.C., Frederick, M.O., Burtoloso, A., Denton, R.M., Rivas, F., Cole, K.P., Aversa, R.J., Gibe, R., Umezawa, T. and Suzuki, T. (2008) J. Am. Chem. Soc., 130, 7466-7476
261. Nicolaou, K.C., Cole, K.P., Frederick, M.O., Aversa, R.J. and Denton, R.M. (2007) Angew. Chem. Int. Ed., 46, 8875-8879
262. See also: Singh, V., Singh, V. (2009) Tetrahedron Lett., 50, 3092-3094
263. Robertson, J., Stevens, K. and Naud, S. (2008) Synlett, 2083-2086
264. Akaike, H., Horie, H., Kato, K. and Akita, H. (2008) Tetrahedron Asymmetry, 19, 1100-1105
265. Guo, H. and O'Doherty, G.A. (2006) Org. Lett., 8, 1609-1612
266. Crawford, C., Nelson, A. and Patel, I. (2006) Org. Lett., 8, 4231-4234
267. Robertson, J., Meo, P., Dallimore, J.W.P., Doyle, B.M. and Hoarau, C. (2004) Org. Lett., 6, 3861-3863
268. Li, M., Scott, J. and O'Doherty, G.A. (2004) Tetrahedron Lett., 45, 1005-1009
269. Li, M. and O'Doherty, G.A. (2004) Tetrahedron Lett., 45, 6407-6411
270. Haukas, M.H. and O'Doherty, G.A. (2002) Org. Lett., 4, 1771-1774
271. Harris, J.M. and O'Doherty, G.A. (2000) Org. Lett., 2, 2983-2986
272. Haukaas, M.H. and O'Doherty, G.A. (2001) Org. Lett., 3, 401-404
273. Balachari, D. and O'Doherty, G.A. (2000) Org. Lett., 2, 4033-4036
274. Taniguchi, T., Takeuchi, M. and Ogasawara, K. (1998) Tetrahedron Asymmetry, 9, 1451-1456
275. De Mico, A., Margarita, R. and Piancatelli, G. (1995) Tetrahedron Lett., 33, 3553-3556
276. Martin, S.F., Lee, W.C., Pacofsky, G.J., Gist, R.P. and Mulhern, T.A. (1994) J. Am. Chem. Soc., 116, 4674-4688
277. Martin, S.F. and Zinke, P.W. (1991) J. Org. Chem., 56, 6606-6611
278. Martin, S.F., Pacofsky, G.J., Gist, R.P. and Lee, W.C. (1989) J. Am. Chem. Soc., 111, 7634-7636.
279. Aza-Achmatowicz to lactams: Leverett, C.A., Cassidy, M.P. and Padwa, A. (2006) J. Org. Chem., 71, 8591-8601
280. Cassidy, M.P. and Padwa, A. (2004) Org. Lett., 6, 4029-4031
281. Harris, J.M. and Padwa, A. (2003) J. Org. Chem., 68, 4371-4381
282. See also: Zhang, H.X., Xia, P. and Zhou, W.S. (2003) Tetrahedron, 59, 2015-2020
283. Yang, C., Liao, L., Xu, Y., Zhang, H., Xia, P. and Zhou, W. (1999) Tetrahedron Asymmetry, 10, 2311-2318.
284. Achmatowicz to polyenes: Kobayashi, Y., Kumar, G.B., Kurachi, T., Acharya, H.P., Yamazaki, T. and Kitazume, T. (2001) J. Org. Chem., 66, 2011-2018
285. See also: Hayashi, Y., Shoji, M., Ishikawa, H., Yamaguchi, J., Tamura, T., Imai, H., Nishigaya, Y., Takabe, K., Kakeya, H. and Osada, H. (2008) Angew. Chem. Int. Ed., 47, 6657-6660
286. Raczko, J. (2003) Tetrahedron, 59, 10181-10186
287. Kobayashi, Y. and Wang, Y.G. (2002) Tetrahedron Lett., 43, 4381-4384
288. Lee, W.W., Shin, H.J. and Chang, S. (2001) Tetrahedron Asymmetry, 12, 29-31
289. Kobayashi, Y., Kumar, B.G. and Kurachi, T. (2000) Tetrahedron Lett., 41, 1559-1563
290. Singlet oxygen: Tofi, M., Montagnon, T., Georgiou, T. and Vassilikogiannakis, G. (2007) Org. Biomol. Chem., 5, 772-777
291. Vassilikogiannakis, G., Margaros, I., Montagnon, T. and Stratakis, M. (2005) Chem. Eur. J., 11, 5899-5907
292. Helliwell, M., Karim, S., Parmee, E.R. and Thomas, E.J. (2005) Org. Biomol. Chem., 3, 3636-3653
293. See also: Georgiou, T., Tofi, M., Montagnon, T. and Vassilikogiannakis, G. (2006) Org. Lett., 8, 1945-1948
294. Sofikiti, N., Tofi, M., Montagnon, T., Vassilikogiannakis, G. and Stratakis, M. (2005) Org. Lett., 7, 2357-2359
295. García, I., Gómez, G., Teijeira, M., Terán, C. and Fall, Y. (2006) Tetrahedron Lett., 47, 1333-1335
296. Teijeira, M., Suárez, P.L., Gómez, G., Terán, C. and Fall, Y. (2005) Tetrahedron Lett., 46, 5889-5892
297. Pérez, M., Canoa, P., Gómez, G., Terán, C. and Fall, Y. (2004) Tetrahedron Lett., 45, 5207-5209
298. Shimazawa, R., Suzuki, T., Dodo, K. and Shirai, R. (2004) Bioorg. Med. Chem., 14, 3291-3294
299. de la Torre, M.C., García, I. and Sierra, M.A. (2002) J. Nat. Prod., 65, 661-668
300. Imamura, P.M. and Costa, M. (2000) J. Nat. Prod., 63, 1623-1625
301. Shiraki, R., Sumino, A., Tadano, K.I. and Ogawa, S. (1996) J. Org. Chem., 61, 2845-2852
302. Parmee, E.R., Mortlock, S.V., Stacey, N.A., Thomas, E.J. and Mills, O.S. (1997) J. Chem. Soc. Perkin Trans. 1, 381-390
303. Electrooxidation: Miller, A.K., Hughes, C.C., Kennedy-Smith, J.J., Gradi, S.N. and Trauner, D. (2006) J. Am. Chem. Soc., 128, 17057-17062
304. Mihelcic, J. and Moeller, K.D. (2003) J. Am. Chem. Soc., 125, 36-37
305. See also: Wu, H. and Moeller, K.D. (2007) Org. Lett., 9, 4599-4602
306. Nieto -Mendoza, E., Guevara-Salazar, J.A., Ramírez-Apan, M.T., Frontana-Uribe, B.A., Cogordan, J.A. and Cárdenas, J. (2005) J. Org. Chem., 70, 4538-4541
307. Sperry, J.B., Constanzo, J.R., Jasinski, J., Butcher, R.J. and Wright, D.L. (2005) Tetrahedron Lett., 46, 2789-2793.
308. Oxidation to acid with RuO 4: Ainai, T., Wang, Y.G., Tokoro, Y. and Kobayashi, Y. (2004) J. Org. Chem., 69, 655-659
309. See also: Liu, L.X., Peng, Q.L. and Huang, P.Q. (2008) Tetrahedron Asymmetry, 19, 1200-1203
310. Aggarwal, V.A. and Vasse, J.L. (2003) Org. Lett., 5, 3987-3990
311. See also: Luo, Y.C., Zhang, H.H., Liu, Y.Z., Cheng, R.L. and Xu, P.F. (2009) Tetrahedron Asymmetry, 20, 1174-1180
312. Krüger, J. and Carreira, E.M. (1998) J. Am. Chem. Soc., 120, 837-838
313. Pagenkopf, B.L., Krüger, J., Stojanovic, A. and Carreira, E.M. (1998) Angew. Chem. Int. Ed. Engl., 37, 3124-3126
314. Dondoni, A., Franco, S., Junquera, F., Merchán, F.L., Merino, P. and Tejero, T. (1997) J. Org. Chem., 62, 5497-5507
315. Kobayashi, Y., Nakano, M. and Okui, H. (1997) Tetrahedron Lett., 38, 8883-8886
316. Other oxidations: Chen, I.C., Wu, Y.K., Liu, H.J. and Zhu, J.L. (2008) Chem. Commun., 4720-4722
317. Watanabe, T., Ohashi, Y., Yoshino, R., Komano, N., Eguchi, M., Maruyama, S. and Ishikawa, T. (2003) Org. Biomol. Chem., 1, 3024-3032.
318. Furans as electrophiles: Meulemans, T.M., Stork, G.A., Macaev, F.Z., Jansen, B.J.M. and De Groot, A. (1999) J. Org. Chem., 64, 9178-9188
319. Hori, K., Hikage, N., Inagaki, A., Mori, S., Nomura, K. and Yoshii, E. (1992) J. Org. Chem., 57, 2888-2902
320. Hori, K., Kazuno, H., Nomura, K. and Yoshii, E. (1993) Tetrahedron Lett., 34, 2183-2186.
321. Furans as nucleophiles (TMSOF): Bardají, G.G., Cantó, M., Alibés, R., Bayón, P., Busqué, F., de March, P., Figueredo, M. and Font, J. (2008) J. Org. Chem., 73, 7657-7662
322. Alibes, R., Bayon, P., de March, P., Figueredo, M., Font, J., García-García, E. and González -Gálvez, D. (2005) Org. Lett., 7, 5107-5109
323. Liras, S., Lynch, C.L., Fryer, A.M., Vu, B.T. and Martin, S.F. (2001) J. Am. Chem. Soc., 123, 5918-5924
324. Rassu, G., Auzzas, L., Zambrano, V., Burreddu, P., Pinna, L., Battistini, L., Zanardi, F. and Casiraghi, G. (2004) J. Org. Chem., 69, 1625-1628.
325. For other examples of TMSOF as nucleophiles see: Snider, B.B. and Che, Q. (2004) Org. Lett., 6, 2877-2880
326. Zanardi, F., Battistini, L., Rassu, G., Auzzas, L., Pinna, L., Marzocchi, L., Acquotti, D. and Casiraghi, G. (2000) J. Org. Chem., 65, 2048-2064
327. Rassu, G., Auzzas, L., Pinna, L., Battistini, L., Zanardi, F., Marzocchi, L., Acquotti, D. and Casiraghi, G. (2000) J. Org. Chem., 65, 6307-6318
328. Rassu, G., Pinna, L., Spanu, P., Zanardi, F., Battistini, L. and Casiraghi, G. (1997) J. Org. Chem., 62, 4513-4517
329. Martin, S.F., Barr, K.J., Smith, D.W. and Bur, S.K. (1999) J. Am. Chem. Soc., 121, 6990-6997
330. Mukai, C., Hirai, S., Kim, I.J., Kido, M. and Hanaoka, M. (1996) Tetrahedron, 52, 6547-6565
331. Furan as nucleophile: Shanmugham, M.S. and White, J.D. (2004) Chem. Commun., 44-45
332. Boyer, F.D., Descoins, C.L., Thanh, G.V., Descoins, C., Prangé, T. and Ducrot, P.H. (2003) Eur. J. Org. Chem., 1172-1183
333. Rose, M.D., Cassidy, M.P., Rashatasakhon, P. and Padwa, A. (2007) J. Org. Chem., 72, 538-549
334. Nilson, M.G. and Funk, R.L. (2006) Org. Lett., 8, 3833-3836
335. Marion, F., Williams, D.E., Patrick, B.O., Hollander, I., Mallon, R., Kim, S.C., Roll, D.M., Fieldberg, L., Van Soest, R. and Andersen, R.J. (2006) Org. Lett., 8, 321-324.
336. For other examples of furans as nucleophiles see: Cassidy, M.P., Özdemir, A.D. and Padwa, A. (2005) Org. Lett., 7, 1339-1342
337. Mal, S.K., Kar, G.K. and Ray, J.K. (2004) Tetrahedron, 60, 2805-2811
338. Padwa, A., Heidelbaugh, T.M., Kuethe, J.T., McClure, M.S. and Wang, Q. (2002) J. Org. Chem., 67, 5928-5937
339. Inone, M., Carson, M.W., Frontier, A.J. and Danishefsky, S.J. (2001) J. Am. Chem. Soc., 123, 1878-1889
340. Sasaki, S., Hamada, Y. and Shiori, T. (1997) Tetrahedron Lett., 38, 3013-3016
341. Jung, M.E. and Siedem, C.S. (1993) J. Am. Chem. Soc., 115, 3822-3823.
342. Cyclopropanations: Kashin, D., Meyer, A., Wittenberg, R., Schöning, K.U., Kamlage, S. and Kirschning, A. (2007) Synthesis, 304-319
343. Chhor, R.B., Nosse, B., Sörgel, S., Böhm, C., Seitz, M. and Reiser, O. (2003) Chem. Eur. J., 9, 260-270
344. Hughes, C.C., Kennedy-Smith, J.J. and Trauner, D. (2003) Org. Lett., 5, 4113-4115
345. Foot, J.S., Phillis, A.T., Sharp, P.P., Willis, A.C. and Banwell, M.G. (2006) Tetrahedron Lett., 47, 6817-6820.
346. [2[] + 2] cycloadditions: de March, P., Figueredo, M., Font, J., Raya, J., Alvarez-Larena, A. and Piniella, J.F. (2003) J. Org. Chem., 68, 2437-2447
347. Crimmins, M.T., Pace, J.M., Nantermet, P.G., Kim-Meade, A.S., Thomas, J.B., Watterson, S.H. and Wagman, A.S. (2000) J. Am. Chem. Soc., 122, 8453-8463.
348. Vasella, A. and Voeffray, R. (1982) Helv. Chim. Acta, 65, 1134-1144
349. Padwa, A. and Price, A.T. (1998) J. Org. Chem., 63, 556-565
350. Padwa, A. and Price, A.T. (1995) J. Org. Chem., 60, 6258-6259
351. Padwa, A., Lynch, S.M., Mejía-Oneto, J.M. and Zhang, H. (2005) J. Org. Chem., 70, 2206-2218
352. Elliott, G.I., Velcicky, J., Ishikawa, H., Li, Y.K. and Boger, D.L. (2006) Angew. Chem. Int. Ed., 45, 620-622.
353. Padwa, A. and Pearson, W.H. (2003) Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry: Towards Heterocycles and Natural Products, Series: Chemistry of Heterocyclic Compounds, vol. 59, John Wiley & Sons, Inc., Hoboken, USA. ISBN: 0-471-28061-5
354. Sessions, E.H., O'Connor, R.T., Jr. and Jacobi, P.A. (2007) Org. Lett., 9, 3221-3224
355. Jacobi, P.A. and Lee, K. (2000) J. Am. Chem. Soc., 122, 4295-4303
356. Sessions, E.H. and Jacobi, P.A. (2006) Org. Lett., 8, 4125-4128
357. Hodgson, D.M., Le Strat, F., Avery, T.D., Donohue, A.C. and Bruckl, T. (2004) J. Org. Chem., 69, 8796-8803
358. Ou, L., Hu, Y., Song, G. and Bai, D. (1999) Tetrahedron, 55, 13999-14004
359. Padwa, A., Brodney, M.A., Marino, J.P., Jr., Osterhout, M.H. and Price, A.T. (1997) J. Org. Chem., 62, 67-77
360. Padwa, A., Brodney, M.A., Marino, J.P., Jr. and Sheenan, S.M. (1997) J. Org. Chem., 62, 78-87
361. Sheenan, S.M. and Padwa, A. (1997) J. Org. Chem., 62, 438-439
362. Kuethe, J.T. and Padwa, A. (1997) J. Org. Chem., 62, 774-775
363. Cochran, J.E. and Padwa, A. (1995) J. Org. Chem., 60, 3938-3939.
364. [3[] + 2] cycloadditions with quinones: Zhou, G. and Corey, E.J. (2005) J. Am. Chem. Soc., 127, 11958-11959
365. See also: Souza, F.E. and Rodrigo, R. (1999) Chem. Commun., 1947-1948
366. Carlini, R., Higgs, K., Older, C., Randhawa, S. and Rodrigo, R. (1997) J. Org. Chem., 62, 2330-2331
367. Brimble, M.A., Nairn, M.R. and Park, J.S.O. (2000) J. Chem. Soc. Perkin Trans. 1, 697-709
368. Brimble, M.A. and Brenstrum, T.J. (2001) J. Chem. Soc. Perkin Trans. 1, 1624-1634
369. Berand, D., Jean, A. and Canesi, S. (2007) Tetrahedron Lett., 48, 8238-8241.
370. Diels-Alder: Brimble, M.A., Duncalf, L.J. and Phythian, S.J. (1997) J. Chem. Soc. Perkin Trans. 1, 1399-1403
371. Aceña, J.L., Arjona, O. and Plumet, J. (1997) J. Org. Chem., 20, 3360-3364
372. Shoji, M., Imai, H., Mukaida, M., Sakai, K., Kakeya, H., Osada, H. and Hayashi, Y. (2005) J. Org. Chem., 70, 79-91
373. Padwa, A. and Ginn, J.D. (2005) J. Org. Chem., 70, 5197-5206
374. Wolkenberg, S.E. and Boger, D.L. (2002) J. Org. Chem., 67, 7361-7364
375. Winkler, J.D., Quinn, K.J., MacKinnon, C.H., Hiscock, S.D. and McLaughlin, E.C. (2003) Org. Lett., 5, 1805-1808
376. Zhang, H., Boonsombat, J. and Padwa, A. (2007) Org. Lett., 9, 279-282
377. Toró, A. and Deslongchamps, P. (2003) J. Org. Chem., 68, 6847-6852
378. Toró, A., L'Heureux, A. and Deslongchamps, P. (2000) Org. Lett., 2, 2737-2740
379. Sutherland, H.S., Souza, F.E.S. and Rodrigo, R.G.A. (2001) J. Org. Chem., 66, 3639-3641.
380. Other Diels-Alder, with 2-amino or 2-thiofurans as substrates: Padwa, A. and Wang, Q. (2006) J. Org. Chem., 71, 7391-7402
381. Wang, Q. and Padwa, A. (2006) Org. Lett., 8, 601-604
382. Padwa, A., Bur, S.K. and Zhang, H. (2005) J. Org. Chem., 70, 6833-6841
383. Padwa, A., Brodney, M.A., Lynch, S.M., Rashatasakhon, P., Wang, Q. and Zhang, H. (2004) J. Org. Chem., 69, 3735-3745
384. Wang, Q. and Padwa, A. (2004) Org. Lett., 6, 2189-2192
385. Takadoi, M., Yamaguchi, K. and Terashima, S. (2003) Bioorg. Med. Chem., 11, 1169-1186
386. Padwa, A., Ginn, J.D., Bur, S.K., Eidell, C.K. and Lynch, S.M. (2002) J. Org. Chem., 67, 3412-3424
387. Padwa, A., Dimitroff, M. and Liu, B. (2000) Org. Lett., 2, 3233-3235.
388. Cyclotrimerizations: Anderson, E.A., Alexanian, E.J. and Sorensen, E.J. (2004) Angew. Chem. Int. Ed., 43, 1998-2001.
389. Recent examples of IMDAF and related cycloadditions: Zubkov, F.I., Ershova, J.D., Orlova, A.A., Zaytsev, V.P., Nikitina, E.V., Peregudov, A.S., Gurbanov, A.V., Borisov, R.S., Khrustalev, V.N., Maharramov, A.M. and Varlamov, A.V. (2009) Tetrahedron, 65, 3789-3803
390. Nielsen, L.B., Slamet, R. and Wege, D. (2009) Tetrahedron, 65, 4569-4577
391. Gao, S., Wang, Q. and Chen, C. (2009) J. Am. Chem. Soc., 131, 1410-1412
392. Quiroz-Florentino, H., Aguilar, R., Santoyo, B.M., Díaz, F. and Tamariz, J. (2008) Synlett, 1023-1028
393. Sarang, P.S., Yadav, A.A., Patil, P.S., Krishna, U.M., Trivedi, G.K. and Salunkhe, M.M. (2007) Synthesis, 1091-1095
394. Brubaker, J.D. and Myers, A.G. (2007) Org. Lett., 9, 3523-3525
395. Chittiboyina, A.G., Kumar, G.M., Carvalho, P.D., Liu, Y., Zhou, Y.D., Nagle, D.G. and Avery, M.A. (2007) J. Med. Chem., 50, 6299-6302
396. Li, C.C., Wang, C.H., Liang, B., Zhang, X.H., Deng, L.J., Liang, S., Chen, J.H., Wu, Y.D. and Yang, Z. (2006) J. Org. Chem., 71, 6892-6897
397. Merten, J., Hennig, A., Schwab, P., Fröhlich, R., Tokalov, S.V., Gutzeit, H.O. and Metz, P. (2006) Eur. J. Org. Chem., 1144-1161
398. Parsons, P.J., Board, J., Waters, A.J., Hitchcock, P.B., Wakenhut, F. and Walter, D.S. (2006) Synlett, 3243-3246
399. Li, C.C., Liang, S., Zhang, X.H., Xie, Z.X., Chen, J.H., Wu, Y.D. and Yang, Z. (2005) Org. Lett., 7, 3709-3712
400. Baba, Y., Hirukawa, N. and Sodeoka, M. (2005) Bioorg. Med. Chem., 13, 5164-5170
401. Pedrosa, R., Sayalero, S., Vicente, M. and Casado, B. (2005) J. Org. Chem., 70, 7273-7278
402. Du, X., Chu, H.V. and Kwon, O. (2004) Tetrahedron Lett., 45, 8843-8846
403. Du, X., Chu, H.V. and Kwon, O. (2003) Org. Lett., 5, 1923-1926
404. Baran, A., Kazaz, C., Se ç en, H. and Sütbeyaz, Y. (2003) Tetrahedron, 59, 3643-3648
405. Fokas, D., Patterson, J.E., Slobodkin, G. and Baldino, C.M. (2003) Tetrahedron Lett., 44, 5137-5140.
406. For other interesting examples of IMDAF and related cycloadditions: Claeys, S., Van Haver, D., De Clercq, P.J., Milanesio, M. and Viterbo, D. (2002) Eur. J. Org. Chem., 1051-1062
407. Lautens, M., Colucci, J.T., Hiebert, S., Smith, N.D. and Bouchain, G. (2002) Org. Lett., 4, 1879-1882
408. Richter, F., Bauer, M., Pérez, C., Maichle-Mössmer, C. and Maier, M.E. (2002) J. Org. Chem., 67, 2474-2480
409. Arjona, O., Menchaca, R. and Plumet, J. (2001) Org. Lett., 3, 107-109
410. Arjona, O., Menchaca, R. and Plumet, J. (2001) J. Org. Chem., 66, 2400-2413
411. Aceña, J.L., Arjona, O., León, M.L. and Plumet, J. (2000) Org. Lett., 2, 3683-3686
412. Trembleau, L., Patiny, L. and Ghosez, L. (2000) Tetrahedron Lett., 41, 6377-6381
413. Gilbert, A.M., Miller, R. and Wulff, W.D. (1999) Tetrahedron, 55, 1607-1630
414. Brickwood, A.C., Drew, M.G.B., Harwood, L.M., Ishikawa, T., Marais, P. and Morisson, V. (1999) J. Chem. Soc. Perkin Trans. 1, 913-921
415. Kurosu, M., Marcin, L.R., Grinsteiner, T.J. and Kishi, Y. (1998) J. Am. Chem. Soc., 120, 6627-6628
416. Chen, C.H., Rao, P.D. and Liao, C.C. (1998) J. Am. Chem. Soc., 120, 13254-13255
417. Baba, Y., Sakamoto, T., Soejima, S. and Kanematsu, K. (1994) Tetrahedron, 50, 5645-5658
418. Kanematsu, K., Soejima, S. and Weng, G. (1991) Tetrahedron Letters, 32, 4761-4764.
419. Oxabicycle ring opening: Lautens, M., Faghou, K. and Hiebert, S. (2003) Acc. Chem. Res., 36, 48-58
420. Padwa, A. (2009) J. Org. Chem., 74, 6421-6441.
421. Retro Diels-Alder: Klunder, A.J.H., Zhu, J. and Zwanenburg, B. (1999) Transient chirality in retro Diels-alder. Chem. Rev., 99, 1163-1198
422. Neubert, B.J. and Snider, B.B. (2003) Org. Lett., 5, 765-768
423. Bloch, R. and Brillet, C. (1991) Tetrahedron Asymmetry, 2, 797-800
424. Bloch, R., Bortolussi, M., Girard, C. and Seck, M. (1992) Tetrahedron, 48, 453-462.
425. [4[] + 3] cycloadditions: Föhlisch, B., Flogaus, R., Henle, G.H., Sendelbach, S. and Henkel, S. (2006) Eur. J. Org. Chem., 2160-2173
426. Lee, J.C. and Cha, J.K. (2001) J. Am. Chem. Soc., 123, 3243-3246
427. See also: Kim, H. and Hoffmann, H.M.R. (2000) Eur. J. Org. Chem., 2195-2201
428. Harmata, M. and Kahraman, M. (1998) Tetrahedron Lett., 39, 3421-3424.
429. [6[] + 4] cycloaddition: Rigby, J.H. and Chouraqui, G. (2005) Synlett, 2501-2503
430. [8[] + 2] cycloaddition: Zhang, L., Buckingham, C. and Herndon, J.W. (2005) Org. Lett., 7, 1665-1667
431. Luo, Y., Herndon, J.W. and Cervantes-Lee, F. (2003) J. Am. Chem. Soc., 125, 12720-12721.
432. [5[] + 2] cycloadditions with pyrilium ions derived from furans: Wender, P.A., Jesudason, C.D., Nakahira, H., Tamura, N., Tebbe, A.L. and Ueno, Y. (1997) J. Am. Chem. Soc., 119, 12976-12977
433. Tang, B., Bray, C.D. and Pattenden, G. (2006) Tetrahedron Lett., 47, 6401-6404
434. Roethle, P.A. and Trauner, D. (2006) Org. Lett., 8, 345-347
435. Roethle, P.A., Hernandez, P.T. and Trauner, D. (2006) Org. Lett., 8, 5901-5904
436. See also: Wender, P.A., Rice, K.D. and Schnute, M.E. (1997) J. Am. Chem. Soc., 119, 7897-7898
437. Wender, P.A., Bi, F.C., Buschmann, N., Gosselin, F., Kan, C., Kee, J.M. and Ohmura, H. (2006) Org. Lett., 8, 5373-5376
438. Magnus, P. and Ollivier, C. (2002) Tetrahedron Lett., 43, 9605-9609
439. Magnus, P., Waring, M.J., Ollivier, C. and Lynch, V. (2001) Tetrahedron Lett., 42, 4947-4950.
440. Radicals: Holzapfel, C.W. and Williams, D.B.G. (1995) Tetrahedron, 51, 8555-8564
441. Guindeuil, S. and Zard, S.Z. (2006) Chem. Commun., 665-667
442. Crich, D., Hwang, J.T. and Yuan, H. (1996) J. Org. Chem., 61, 6189-6198.
443. Dearomatization via ionic reactions: Yin, B.L., Hu, T.S., Yue, H.J., Gao, Y., Wu, W.M. and Wu, Y.L. (2004) Synlett, 306-310
444. Gao, Y., Wu, W.L., Wu, Y.L., Ye, B. and Zhou, R. (1998) Tetrahedron, 54, 12523-12538
445. Tokumaru, K., Arai, S. and Nishida, A. (2006) Org. Lett., 8, 27-30.
446. Trost, B.M. and Crawley, M.L. (2002) J. Am. Chem. Soc., 124, 9328-9329
447. See also: Meira, P.R.R., Moro, A.V. and Correia, C.R.D. (2007) Synthesis, 2279-2286
448. Trost, B.M. and Kallander, L.S. (1999) J. Org. Chem., 64, 5427-5435.
449. Ireland-Claisen: Ireland, R.E., Armstrong, J.D., III, Lebreton, J., Meissner, R.S. and Rizzacasa, M.A. (1993) J. Am. Chem. Soc., 115, 7152-7165
450. Ireland, R.E., Meissner, R.S. and Rizzacasa, M.A. (1993) J. Am. Chem. Soc., 115, 7166-7172
451. See also: Kraus, G.A. and Wei, J. (2004) J. Nat. Prod., 67, 1039-1040.
452. Ring expansion: Kocienski, P., Brown, R.C.D., Pommier, A., Procter, M. and Schmidt, B. (1998) J. Chem. Soc. Perkin Trans. 1, 9-39.
453. Rigidifiers: Felzmann, W., Arion, V.B., Mieusset, J.-L. and Mulzer, J. (2006) Org. Lett., 8, 3849-3851.
454. Ley, S.V., Brown, D.S., Clase, J.A., Fairbanks, A.J., Lennon, I.C., Osborn, H.M.I., Stokes, E.S.E. and Wadsworth, D.J. (1998) J. Chem. Soc. Perkin Trans. 1, 2259-2276
455. See also: Boons, G.-J., Lennon, I.C., Ley, S.V., Owen, E.S.E., Staunton, J. and Wadsworth, D.J. (1994) Tetrahedron Lett., 35, 323-326
456. Hori, K., Kazuno, H., Nomura, K. and Yoshii, E. (1993) Tetrahedron Lett., 34, 2183-2186.
457. Andersen, N.G. and Keay, B.A. (2001) Chem. Rev., 101, 997-1030
458. Wong, O.A. and Shi, Y. (2008) Chem. Rev., 108, 3968-3987
459. See also: Spescha, M. and Rihs, G. (1993) Helv. Chim. Acta, 76, 1219-1230
460. Tuttle, J.B., Ouellet, S.G. and MacMillan, D.W.C. (2006) J. Am. Chem. Soc., 128, 12662-12663
461. Northrup, A.B. and MacMillan, D.W.C. (2002) J. Am. Chem. Soc., 124, 2458-2460.
462. Tadano, K., Isshiki, Y., Minami, M. and Ogawa, S. (1993) J. Org. Chem., 58, 6266-6279
463. Tadano, K., Isshiki, Y., Minami, M. and Ogawa, S. (1992) Tetrahedron Lett., 33, 7899-7902.