Strategies for the synthesis of 2,3-dihydrobenzofurans

Journal of Chemical Research

Volumn 35, Issue 7, 2011, Pages 377-385

  Sheppard, Tom D ^a  

^a UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

catalysis; cyclisation; Dihydrobenzofurans; heterocycles; natural products

Indexed keywords

EID: 80051935927     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/174751911X13096980701749     Document Type: Review

References (89)

1. S.P. Verevkin, V.N. Emel'yanenko, A.A. Pimerzin and E.E. Vishnevskaya, J. Phys. Chem. A, 2011, 115, 1992.
2. I.S. Lee, H.-J. Kim, U.-J. Youn, Q.-C. Chen, J.-P. Kim, D.T. Ha, T.M. Ngoc, B.-S. Min, S.-M. Lee, H.-J. Jung, M.-K. Na and K.-H. Bae, Helv. Chim. Act., 2010, 93, 272.
3. W.-S. Feng, X.-Y. Zang, X.-K. Zheng, Y.-Z. Wang, H. Chen and Z. Li, J. Asian Nat. Prod. Res., 2010, 12, 557.
4. P.X. Lai, Q.L. Ma and K.H. Row, J. Chem. Res., 2010, 514.
5. S.K. Manna, J.S. Bose, V. Gangan, N. Raviprakash, T. Navaneetha, P.B. Raghavendra, B. Babajan, C.S. Kumar and S.K. Jain, J. Biol. Chem., 2010, 285, 22318.
6. D.T. Ha, T.M. Ngoc, I. Lee, Y.M. Lee, J.S. Kim, H. Jung, S. Lee, M. Na and K. Bae, J. Nat. Prod., 2009, 72, 1465.
7. E.D. Coy, L.E. Cuca and M. Sefkow, Bioorg. Med. Chem. Lett., 2009, 19, 6922.
8. S. Shang and S. Long, Chem. Nat. Compounds, 2008, 44, 186.
9. J.-A. Duan, L. Wang, S. Qian, S. Su and Y. Tang, Arch. Pharmacol Res., 2008, 31, 965.
10. S. Di Micco, F. Mazué, C. Daquino, C. Spatafora, D. Delmas, N. Latruffe, C. Tringali, R. Riccio and G. Bifulco, Org. Biomol. Chem., 2011, 9, 701.
11. H.-Y. Huang, T. Ishikawa, C.-F. Peng, I.-L. Tsai and I.-S. Chen, J. Nat. Prod., 2008, 71, 1146.
12. H. Zhang, S. Qiu, P. Tamez, G. T. Tan, Z. Aydogmus, N. Van Hung, N.M. Cuong, C. Angerhofer, D.D. Soejarto, J.M. Pezzuto and H.H.S. Fong, Pharm. Biol., 2002, 40, 221.
13. M. Saito, M. Ueo, S. Kametaka, O. Saigo, S. Uchida, H. Hosaka, K. Sakamoto, T. Nakahara, A. Mori and K. Ishii, Biolog. Pharm. Bull., 2008, 31, 1959.
14. S.F. Kouam, S.N. Khan, K. Krohn, B.T. Ngadjui, D.G.W.F. Kapche, D.B. Yapna, S. Zareem, A.M.Y. Moustafa and M.I. Choudhary, J. Nat. Prod., 2006, 69, 229.
15. T. Wakimoto, K. Miyata, H. Ohuchi, T. Asakawa, H. Nukaya, Y. Suwa and T. Kan, Org. Lett., 2011, 13, 2789.
16. A. Stoessl, Tetrahedron Lett., 1966, 7, 2849.
17. A. Stoessl, Tetrahedron Lett., 1966, 7, 2287.
18. Y.-W. Chin, H.-B. Chai, W.J. Keller and A.D. Kinghorn, J. Agric. Food Chem., 2008, 56, 7759.
19. Z. Huang, Q. Cui, L. Xiong, Z. Wang, K. Wang, Q. Zhao, F. Bi and Q. Wang, J. Agric. Food Chem., 2009, 57, 2447-2456.
20. N. Negoro, S. Sasaki, S. Mikami, M. Ito, M. Suzuki, Y. Tsujihata, R. Ito, A. Harada, K. Takeuchi, N. Suzuki, J. Miyazaki, T. Santou, T. Odani, N. Kanzaki, M. Funami, T. Tanaka, A. Kogame, S. Matsunaga, T. Yasuma and Y. Momose, Acs Med. Chem. Lett., 2010, 1, 290-294.
21. W. Chen, X.-D. Yang, Y. Li, L.-J. Yang, X.-Q. Wang, G.-L. Zhang and H.-B. Zhang, Org. Biomol Chem., 2011, DOI: 10.1039/C1OB05116D.
22. R.P. Tripathi, A.K. Yadav, A. Ajay, S.S. Bisht, V. Chaturvedi and S.K. Sinha, Eur. J. Med. Chem., 2010, 45, 142.
23. S. Van Miert, S. Van Dyck, T.J. Schmidt, R. Brun, A. Vlietinck, G. Lemiere and L. Pieters, Biorg. Med Chem. 2005, 13, 661.
24. J.E. Frampton, Drugs, 2009, 69, 2463
25. C.B. Chapleo, P.L. Myers, R.C.M. Butler, J.A. Davis, J.C. Doxey, S.D. Higgins, M. Myers, A.G. Roach, C.F.C. Smith, J. Med. Chem., 1984, 27, 570.
26. F. Bertolini and M. Pineschi, Org. Prep. Proc. Int., 2009, 41, 385.
27. H. Jiang, T. Sugiyama, A. Hamajima and Y. Hamada, Adv. Synth. Catal., 2011, 353, 155.
28. A. Chatterjee and S.S. Mitra, J. Am. Chem. Soc., 1949, 71, 606.
29. S.K. Dinda, S.K. Das and G. Panda, Synthesis, 2009, 1886.
30. F.A. Macías, R.M. Varela, A. Torres and J.M.G. Molinillo, J. Nat. Prod., 1999, 62, 1636.
31. S.K. Das and G. Panda, Tetrahedron, 2008, 64, 4162-4173.
32. C. Ito, S. Katsuno, Y. Kondo, H.T.-W. Tan and H. Furukawa, Chem. Pharm. Bull., 2000, 48, 339.
33. J. Takashima and A. Ohsaki, J. Nat. Prod., 2002, 65, 1843.
34. S. Kantevari, D. Addla and B. Sridhar, Synthesis, 2010, 3745.
35. J. Seo, S.S. Lee, W.-T. Gong and K. Hiratani, Tetrahedron Lett., 2008, 49, 3770.
36. K. Okuma, T. Yasuda, I. Takeshita, K. Shioji and Y. Yokomori, Tetrahedron, 2007, 63, 8250.
37. B.S. Samant and S.S. Bhagwat, Chinese J. Catal., 2011, 32, 231.
38. Q.Z. Zhou, C.L. He and Z.C. Chen, Chinese Chem. Lett., 2008, 19, 661.
39. B. Gabriele, R. Mancuso and G. Salerno, J. Org. Chem., 2008, 73, 7336.
40. J. Mangas-Sánchez, E. Busto, V Gotor-Fernández and V Gotor, Org. Lett., 2010, 12, 3498.
41. M. Uyanik, H. Okamoto, T. Yasui and K. Ishihara, Science, 2010, 328, 1376-1379.
42. S.-I. Kuwabe, K.E. Torraca and S.L. Buchwald, J. Am. Chem. Soc., 2001, 123, 12202.
43. M. Palucki, J.P. Wolfe and S.L. Buchwald, J. Am. Chem. Soc., 1996, 118, 10333.
44. C. Pan, Z. Ma, J. Yu, Z. Zhang, A. Hui and Z. Wang, Synlett, 2005, 1922.
45. J. Zhu, B.A. Price, S.X. Zhao and P.M. Skonezny, Tetrahedron Lett., 2000, 41, 4011.
46. C. Körner, P. Starkov and T.D. Sheppard, J. Am. Chem. Soc., 2010, 132, 5968.
47. J.X. Qiao and P.Y.S. Lam, Synthesis, 2010, 829.
48. X. Wang, Y. Lu, H.-X. Dai and J.-Q. Yu, J. Am. Chem. Soc., 2010, 132, 12203.
49. Y. Komine, A. Kamisawa and K. Tanaka, Org. Lett., 2009, 11, 2361.
50. J.E. Imbriglio and J.D. Rainier, Tetrahedron Lett, 2001, 42, 6987.
51. T. Mino, Y. Naruse, S. Kobayashi, S. Oishi, M. Sakamoto and T. Fujita, Tetrahedron Lett., 2009, 50, 2239.
52. B.M. Trost, D.A. Brinhley and S.M. Silverman, J. Am. Chem. Soc., 2011, DOI: 10.1021/ja201181g.
53. C. Fressigné, A.-L. Girard, M. Durandetti and J. Maddaluno, Chem. \- A Eur. J., 2008, 14, 5159.
54. H. Sundén and R. Olsson, Org. Biomol. Chem., 2010, 8, 4831.
55. F.A. Siqueira, J.G. Taylor and C.R.D. Correia, Tetrahedron Lett., 2010, 51, 2102.
56. M. Szlosek-Pinaud, P. Diaz, J. Martinez and F. Lamaty, Tetrahedron, 2007, 63, 3340.
57. H.S. Lee, K.H. Kim, J.W. Lim and J.N. Kim, Bull. Korean Chem. Soc., 2011, 32, 1083.
58. H.M.L. Davies and T. Hansen, J. Am. Chem. Soc., 1997, 119, 9075.
59. H.M.L. Davies, T. Hansen and M.R. Churchill, J. Am. Chem. Soc., 2000, 122, 3063.
60. H.M.L. Davies, M.VA. Grazini and E. Aouad, Org. Lett., 2001, 3, 1475.
61. W. Kurosawa, T. Kan and T. Fukuyama, Synlett, 2003, 1028.
62. Y. Natori, H. Tsutsui, N. Sato, S. Nakamura, H. Nambu, M. Shiro and S. Hashimoto, J. Org. Chem., 2009, 74, 4418.
63. T. Hayashi and R.H. Thomson, Phytochemistry, 1975, 14, 1085.
64. P.J.C. Benevides, P. Sartorelli and M.J. Kato, Phytochemistry, 1999, 52, 339.
65. Y. Koizumi, H. Kobayashi, T. Wakimoto, T. Furuta, T. Fukuyama and T. Kan, J. Am. Chem. Soc., 2008, 130, 16854.
66. H. Sato, H. Kawagishi, T. Nishimura, S. Yoneyama, Y. Yoshimoto, S. Sakamura, A. Furusaki, S. Katsuragi and T. Matsumoto, Agric. Biol. Chem., 1985, 49, 2969.
67. D.-H. Wang and J.-Q. Yu, J. Am. Chem. Soc., 2011, 133, 5767.
68. D. Belmessieri, L.C. Morrill, C. Simal, A.M.Z. Slawin and A.D. Smith, J. Am. Chem. Soc., 2011, 133, 2714.
69. A. Capperucci, A. Degl'Innocenti, T. Nocentini and S. Pollicino, J. Sulfur Chem., 2009, 30, 319.
70. R. Pérez-Ruiz, O. Hinze, J.-M. Neudofl, D. Blunk, H. Görner and A.G. Griesbeck, Photochem. Photobiol. Sci., 2008, 7, 782.
71. P. Xie, Y Huang and R. Chen, Org. Lett., 2010, 12, 3768.
72. R.V. Rozhkov and R.C. Larock, J. Org. Chem., 2010, 75, 4131.
73. E.D. Coy, L. Jovanovic and M. Sefkow, Org. Lett., 2010, 12, 1976.
74. E.D. Coy, L.E. Cuca and M. Sefkow, Org. Biomol. Chem., 2010, 8, 2003.
75. S.M.O. Van Dyck, G.L.F. Lemière, T.H.M. Jonckers and R. Dommisse, Molecules, 2000, 5, 153.
76. L. Pieters, S. Van Dyck, M. Gao, R. Bai, E. Hamel, A. Vlietinck and G. Lemière, J. Med Chem. 1999; 42: 5475.
77. C. Daquino, A. Rescifina, C. Spatafora and C. Tringali, Eur. J. Org. Chem., 2009, 6289.
78. S. Moussouni, M.-L. Saru, E. Ioannou, M. Mansour, A. Detsi, V Roussis and P. Kefalas, Tetrahedron Lett., 2011, 52, 1165.
79. M. Shi, X.-Y. Tang and Y-H. Yang, J. Org. Chem., 2008, 73, 5311.
80. T. Lomberget and R. Barret, Tetrahedron Lett., 2008, 49, 715.
81. K. Kokubo, K. Harada, E. Mochizuki and T. Oshima, Tetrahedron Lett., 2010, 51, 955.
82. VV Kouznetsov, D.R.M. Arenas and A.R.R. Bohórquez, Tetrahedron Lett., 2008, 49, 3097.
83. R.-V. Nguyen and C.-J. Li, Synlett, 2008, 1897.
84. M. Mascal, K.V. Modes and A. Durmus, Angew. Chem. Int. Ed., 2011, 10.1002/anie.201006423.
85. H. Qin, Z. Xu, Y Cui and Y Jia, Angew. Chem. Int. Ed., 2011, 10.1002/ anie.201100495.
86. A.S.K. Hashmi, M. Rudolph, J.W. Bats, W. Frey, F Rominger and T. Oeser, Chem.-A Eur. J., 2008, 14, 6672.
87. M.S. Khanna, O.V. Singh, C.P. Garg and R.P. Kapoor, Synth. Commun., 1993, 23, 585.
88. J. Meng, T. Jiang, H.A. Bhatti, B.S. Siddiqui, S. Dixon and J.D. Kilburn, Org. Biomol. Chem., 2010, 8, 107.
89. S. Chasset-Boyé, M.C. Viaud-Massuard, F Suzenet and G. Guillaumet, Rev. Chim., 2010, 61, 404.