Efficient synthesis of benzofurans utilizing [3,3]-sigmatropic rearrangement triggered by N-trifluoroacetylation of oxime ethers: Short synthesis of natural 2-arylbenzofurans

European Journal of Organic Chemistry

Volumn , Issue 9, 2007, Pages 1491-1509

  Takeda, Norihiko ^a   Miyata, Okiko ^a   Naito, Takeaki ^a  

^a KOBE PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Benzofuran; Sigmatropic rearrangement; Total synthesis; Trifluoroacetic anhydride; Trifluoroacetyl triflate

Indexed keywords

EID: 34250649345     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200601001     Document Type: Article

References (112)

1. a) C. C. Hughes, D. Trauner, Angew. Chem. Int. Ed. 2002, 41, 1569-1572;
2. b) B. M. Trost, W. Tang, Angew. Chem. Int. Ed. 2002, 41, 2795-2797;
3. c) C. J. Hamilton, A. H. Fairlamb, I. M. Eggleston, J. Chem. Soc., Perkin Trans. 1 2002, 1115-1123;
4. d) J. Li, S. Jeong, L. Esser, P. G. Harran, Angew. Chem. Int. Ed. 2001, 40, 4765-4770;
5. e) K. C. Nicolaou, P. B. Rao, J. Hao, M. V. Reddy, G. Rassias, X. Huang, D. Y.-K. Chen, S. A. Snyder, Angew. Chem. Int. Ed. 2003, 42, 1753-1758;
6. f) A. W. G. Burgett, Q. Li, Q. Wei, P. G. Harran, Angew. Chem. Int. Ed. 2003, 42, 4961-4966;
7. g) J. C. Anderson, R. M. Denton, C. Wilson, Org. Lett. 2005, 7, 123-125;
8. h) G.-N. Zhang, L.-Y. Zhong, S. W. A. Bligh, Y.-L. Guo, C.-F. Zhang, M. Zhang, Z.-T. Wang, L.-S. Xu, Phytochemistry 2005, 66, 1113-1120;
9. i) H. Tanaka, M. Sudo, M. Hirata, M. Sako, M. Sato, I.-S. Chen, T. Fukui, Heterocycles 2005, 65, 871-877;
10. j) B. B. Snider, M. Lobera, Tetrahedron Lett. 2004, 45, 5015-5018;
11. k) M. Doe, T. Shibue, H. Haraguchi, Y. Morimoto, Org. Lett. 2005, 7, 1765-1768;
12. l) J. Boukouvalas, M. Pouliot, J. Robichaud, S. MacNeil, V. Sniekus, Org. Lett. 2006, 8, 3597-3599;
13. m) F. Marion, D. E. Williams, B. O. Patrick, I. Hollander, R. Mallon, S. C. Kim, D. M. Roll, L. Feldberg, R. V. Soest, R. J. Andersen, Org. Lett. 2006, 8, 321-324.
14. For selected examples of synthetic methods of benzofurans, see: a) W. Friedrichsen, in: Comprehensive Heterocyclic Chemistry II, vol. 2 (Eds.: C. W. Bird, A. R. Katritzky, C. W. Rees, E. F. V. Scriven), Pergamon, London, 1996, chapter 2.1, pp. 368-378;
15. b) S. Greve, W. Friedrichsen, Prog. Heterocycl. Chem. 1999, 11, 144-162;
16. c) C. C. Lindsey, K. L. Wu, T. R. R. Pettus, Org. Lett. 2006, 8, 2365-2367;
17. d) R.-V. Nguyen, X. Yao, C.-J. Li, Org. Lett. 2006, 8, 2397-2399;
18. e) C.-Y. Chen, P. G. Dormer, J. Org. Chem. 2005, 70, 6964-6967;
19. f) G. Zhou, E. J. Corey, J. Am. Chem. Soc. 2005, 127, 11958-11959;
20. g) K. Thede, N. Diedrichs, J. P. Ragot, Org. Lett. 2004, 6, 4595-4597;
21. h) D. Yue, T. Yao, R. C. Larock, J. Org. Chem. 2005, 70, 10292-10296;
22. i) A. Fürstner, P. W. Davies, J. Am. Chem. Soc. 2005, 127, 15024-15025;
23. j) I. Nakamura, Y. Mizushima, Y. Yamamoto, J. Am. Chem. Soc. 2005, 127, 15022-15023;
24. k) C. G. Bates, P. Saejueng, J. M. Murphy, D. Venkataraman, Org. Lett. 2002, 4, 4727-4729;
25. l) H. Zhang, E. M. Ferreira, B. M. Stoltz, Angew. Chem. Int. Ed. 2004, 43, 6144-6148;
26. m) S. R. Baker, M. Cases, M. Keenan, R. A. Lewis, P. Tan, Tetrahedron Lett. 2003, 44, 2995-2999.
27. a) T. Sheradsky, Tetrahedron Lett. 1966, 7, 5225-5227;
28. b) A. Mooradical, P. E. Dupont, Tetrahedron Lett. 1967, 8, 2867-2869;
29. c) T. Sheradsky, J. Heterocycl. Chem. 1967, 4, 413-414;
30. d) D. Kaminsky Jr, J. Shavel, R. I. Meltzer, Tetrahedron Lett. 1967, 8, 859-861;
31. e) A. Alemagna, C. Baldoli, P. D. Buttero, E. Licandro, S. Maiorana, J. Chem. Soc., Chem. Commun. 1985, 417-418;
32. f) A. Alemagna, C. Baldoli, P. D. Buttero, E. Licandro, S. Maiorana, Synthesis 1987, 192-196;
33. g) Y. Endo, K. Namikawa, K. Shudo, Tetrahedron Lett. 1986, 27, 4209-4212;
34. h) J.-Y. Laronze, R. E. Boukili, D. Patigny, S. Dridi, D. Cartier, J. Lévy, Tetrahedron 1991, 47, 10003-10014;
35. i) J. Moron, C. Huel, E. Bisagni, Heterocycles 1992, 34, 1353-1364;
36. j) A. J. Castellino, H. Rapoport, J. Org. Chem. 1984, 49, 4399-4404;
37. k) A. J. Castellino, H. Rapoport, J. Org. Chem. 1986, 51, 1006-1011;
38. l) P. R. Guzzo, R. N. Buckle, M. Chou, S. R. Dinn, M. E. Flaugh, A. D. Kiefer Jr, K. T. Ryter, A. J. Sampognaro, S. W. Tregay, Y.-C. Xu, J. Org. Chem. 2003, 68, 770-778.
39. a) O. Miyata, N. Takeda, Y. Morikami, T. Naito, Org. Biomol. Chem. 2003, 1, 254-256;
40. b) O. Miyata, N. Takeda, T. Naito, Org. Lett. 2004, 6, 1761-1763.
41. a) T. Pacher, C. Seger, D. Engelmeier, S. Vajrodaya, O. Hofer, H. Greger, J. Nat. Prod. 2002, 65, 820-827.
42. a) B. F. Bowden, E. Ritchie, W. C. Taylor, Aust. J. Chem. 1972, 25, 2659-2669;
43. b) E. Stahl, I. Ittel, Planta Med. 1981, 42, 144-154;
44. c) B. Freixa, R. Vila, E. A. Ferro, T. Adzet, S. Cañigueral, Planta Med. 2001, 67, 873-875;
45. d) M. Carini, G. Aldíní, M. Oriolí, R. M. Facino, Planta Med. 2002, 68, 193-197;
46. e) D. C. Chauret, C. B. Berrnard, J. T. Arnason, T. J. Durst, J. Nat. Prod. 1996, 59, 152-155.
47. a) R. P. Singh, D. Singh, Heterocycles 1985, 23, 903-907;
48. b) S. B. Pandit, Synth. Commun. 1988, 18, 157-166;
49. c) T. Kappe, Chem. Ber. 1978, 111, 3857-3866.
50. H. M. Petrassi, K. B. Sharpless, J. W. Kelly, Org. Lett. 2001, 3, 139-142.
51. a) O. Miyata, Y. Kimura, K. Muroya, H. Hiramatsu, T. Naito, Tetrahedron Lett. 1999, 40, 3601-3604;
52. b) O. Miyata, Y. Kimura, T. Naito, Chem. Commun. 1999, 2429-2430;
53. c) O. Miyata, Y. Kimura, T. Naito, Synthesis 2001, 1635-1638;
54. d) O. Miyata, N. Takeda, T. Naito, Heterocycles 2002, 57, 1101-1107;
55. e) O. Miyata, N. Takeda, Y. Kimura, Y. Takemoto, N. Tohnai, M. Miyata, T. Naito, Tetrahedron 2006, 62, 3629-3647.
56. a) J. S. Lee, P. L. Fuchs, J. Am. Chem. Soc. 2005, 127, 13122-13123;
57. b) J. Gil, M. Medio-Simon, G. Mancha, G. Asensio, Eur. J. Org. Chem. 2005, 1561-1567;
58. c) J. S. Lee, P. L. Fuchs, Org. Lett. 2003, 5, 3619-3622;
59. d) A. S. Kiselyov, R. G. Harvey, Tetrahedron Lett. 1995, 36, 4005-4008;
60. e) T. R. Forbus Jr, S. L. Taylor, J. C. Martin, J. Org. Chem. 1987, 52, 4156-4159.
61. S. Kim, J.-Y. Yoon, J. Am. Chem. Soc. 1997, 119, 5982-5983.
62. N. Kurono, E. Honda, F. Komatsu, K. Orito, M. Tokuda, Tetrahedron 2004, 60, 1791-1801.
63. a) W. K.-D. Brill, J. Nielsen, M. H. Caruthers, J. Am. Chem. Soc. 1991, 113, 3972-3980;
64. b) R. K. Haynes, C. Indorato, Aust. J. Chem. 1984, 37, 1183-1194.
65. A. Mekhalfia, R. Mutter, W. Heal, B. Chen, Tetrahedron 2006, 62, 5617-5625.
66. TFAT is moisture-sensitive and is readily hydrolyzed to produce TFA and TfOH.
67. When trifluoroacetic anhydride (TFAA) was used, the oxime ether could not give 2-arylbenzofuran.
68. a) R. S. Ward, Nat. Prod. Rep. 1993, 10, 1-28;
69. b) R. S. Ward, Nat. Prod. Rep. 1995, 12, 183-205;
70. c) R. S. Ward, Nat. Prod. Rep. 1997, 14, 43-74;
71. d) A. G. Chittiboyina, Ch. R. Reddy, E. B. Watkins, M. A. Avery, Tetrahedron Lett. 2004, 45, 1689-1691;
72. e) W. Kurosawa, T. Kan, T. Fukuyama, J. Am. Chem. Soc. 2003, 125, 8112-8113;
73. f) I. Muhammad, X.-C. Li, M. R. Jacob, B. L. Tekwani, D. C. Dunbar, D. Ferreira, J. Nat. Prod. 2003, 66, 804-809.
74. J. Y. Pasturel, G. Solladie, J. Maignan, Fr. Demande FR 2833259, 2003 [Chem. Abstr. 2003, 139, 36375].
75. T. Bach, M. Bartels, Synthesis 2003, 925-939.
76. B. A. McKittrick, R. Stevenson, J. Chem. Soc., Perkin Trans. 1 1983, 475-482.
77. a) E. M. Bickoff, A. N. Booth, R. L. Lyman, A. L. Livingston, C. R. Thompson, F. Deeds, Science 1957, 126, 969-970;
78. b) E. M. Bickoff, J. Am. Chem. Soc. 1958, 80, 3969-3971.
79. For selected examples of synthesis of Coumestan, see: a) G. A. Kraus, N. Zhang, J. Org. Chem. 2000, 65, 5644-5646;
80. b) Y. R. Lee, J. Y. Suk, B. S. Kim, Org. Lett. 2000, 2, 1387-1389;
81. c) K. Hiroya, N. Suzuki, A. Yasuhara, Y. Egawa, A. Kasano, T. Sakamoto, J. Chem. Soc., Perkin Trans. 1 2000, 4339-4346;
82. d) R. Laschober, T. Kappe, Synthesis 1990, 387-388.
83. T. Sheradsky, E. Nov, S. Segal, A. Frank, J. Chem. Soc., Perkin Trans. 1 1977, 1827-1831.
84. N. Haga, Y. Endo, K. Kataoka, K. Yamaguchi, K. Shudo, J. Am. Chem. Soc. 1992, 114, 9795-9806.
85. T. Sheradsky, E. Nov, J. Chem. Soc., Perkin Trans. 1 1980, 2781-2786.
86. C. Majdik, Rev. Chim. (Bucharest) 1989, 40, 490-493.
87. A. G. Schultz, J. J. Napier, R. Ravichandran, J. Org. Chem. 1983, 48, 3408-3412.
88. M. Bisagni, N. P. Buu-Hoï, R. Royer, J. Chem. Soc. 1955, 3688-3693.
89. G. W. Kabalka, L. Wang, R. M. Pagni, Tetrahedron 2001, 57, 8017-8028.
90. S. Akiyama, H. Akimoto, S. Nakatsuji, K. Nakashima, Bull. Chem. Soc. Jpn. 1985, 58, 2192-2196.
91. K. Schofield, R. S. Ward, A. M. Choudhury, J. Chem. Soc. 1971, 2834-2837.
92. A. R. Katritzky, X. Lan, Z. Zhang, J. Heterocycl. Chem. 1993, 30, 381-387.
93. H. Naito, S. Kitano, R. Fukumoto, S. Morioka, Jpn. Kokai Tokkyo Koho JP 02048524, 1990 [Chem. Abstr. 1990, 113, 34694w].
94. D. Hellwinkel, K. Göke, Synthesis 1995, 1135-1141.
95. A. Kasahara, T. Izumi, M. Yodono, R. Saito, T. Takeda, T. Sugawara, Bull. Chem. Soc. Jpn. 1973, 46, 1220-1225.
96. K. Eichinger, P. Nussbaumer, Synthesis 1991, 663-664.
97. J. N. Chatterjea, N. M. Sahai, N. C. Jain, J. Indian Chem. Soc. 1970, 47, 261-266.
98. J. Guillaumel, N. Boccara, P. Demerseman, J. Heterocycl. Chem. 1990, 27, 1047-1051.
99. Y. Kawase, Bull. Chem. Soc. Jpn. 1962, 35, 573-577.
100. K. Oishi, K. Kurosawa, Bull. Chem. Soc. Jpn. 1980, 53, 179-184.
101. C. E. Castro, E. J. Gaughan, D. C. Owsley, J. Org. Chem. 1966, 31, 4071-4078.
102. A. Mooradian, P. E. Dupont, J. Heterocycl. Chem. 1967, 4, 441-444.
103. T. Eicher, V. Schneider, Synthesis 1989, 372-378.
104. R. Sanz, M. P. Castroviejo, Y. Fernández, F. J. Fañanas, J. Org. Chem. 2005, 70, 6548-6551.
105. P. Saejueng, C. G. Bates, D. Venkataraman, Synthesis 2005, 1706-1712.
106. W.-M. Dai, K. W. Lai, Tetrahedron Lett. 2002, 43, 9377-9380.
107. R. Stoermer, Ber. Dtsch. Chem. Ges. 1911, 44, 1853-1865.
108. W. Davies, S. Middleton, J. Chem. Soc. 1958, 822-825.
109. G. D. McAllister, R. C. Hartly, M. J. Dawson, A. R. Knaggs, J. Chem. Soc., Perkin Trans. 1 1998, 3453-3458.
110. M. Watanabe, M. Date, K. Kawasaki, T. Hori, S. Furukawa, Chem. Pharm. Bull. 1991, 39, 41-48.
111. K. Nogami, K. Kurosawa, Bull. Chem. Soc. Jpn. 1974, 47, 505-506.
112. C. Majdik, Rev. Chim. (Bucharest) 1989, 40, 689-693.