Lewis acid-promoted synthesis of unsymmetrical and highly functionalized carbazoles and dibenzofurans from biaryl triazenes: Application for the total synthesis of clausine C, clausine R, and clauraila A

Chemistry - A European Journal

Volumn 17, Issue 49, 2011, Pages 13665-13669

  Yang, Weijun ^a   Zhou, Jun ^a   Wang, Binjie ^a   Ren, Hongjun ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

alkaloids; carbazole; dibenzofuran; nucleophilic substitution; regioselectivity; triazene

Indexed keywords

ALKALOIDS; CARBAZOLE; DIBENZOFURANS; NUCLEOPHILIC SUBSTITUTIONS; TRIAZENES;

ELECTROPOLYMERIZATION; METABOLITES; NITROGEN COMPOUNDS; POLYCYCLIC AROMATIC HYDROCARBONS;

REGIOSELECTIVITY;

ALKALOID; BENZOFURAN DERIVATIVE; CARBAZOLE DERIVATIVE; CLAURAILA A; CLAUSINE C; DIBENZOFURAN; LEWIS ACID; TRIAZENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS;

ALKALOIDS; BENZOFURANS; CARBAZOLES; LEWIS ACIDS; MOLECULAR STRUCTURE; TRIAZENES;

EID: 82455192845     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201102802     Document Type: Article

References (98)

1. A. Fürstner, M. M. Domostoj, B. Scheiper, J. Am. Chem. Soc. 2006, 128, 8087-8094
2. P. Buchgraber, M. M. Domostoj, B. Scheiper, C. Wirtz, R. Mynott, J. Rust, A. Fürstner, Tetrahedron 2009, 65, 6519-6534
3. K. Okano, H. Fujiwara, T. Noji, T. Fukuyama, H. Tokuyama, Angew. Chem. 2010, 122, 6061-6065
4. Angew. Chem. Int. Ed. 2010, 49, 5925-5929
5. K. Warabi, S. Matsunaga, R. W. M. van Soest, N. Fusetani, J. Org. Chem. 2003, 68, 2765-2770.
6. Y. Feng, A. R. Carroll, R. Addepalli, G. A. Fechner, V. M. Avery, R. J. Quinn, J. Nat. Prod. 2007, 70, 1790-1792.
7. S. P. Kureel, R. S. Kapil, S. P. Popli, Tetrahedron Lett. 1969, 10, 3857-3862
8. T.-S. Wu, M.-L. Wang, P.-L. Wu, Phytochemistry 1996, 43, 785-789
9. A. Ueno, T. Kitawaki, N. Chida, Org. Lett. 2008, 10, 1999-2002.
10. H.-J. Knölker, K. R. Reddy, in The Alkaloids: Chemistry and Biology, Vol. 65 (Ed.:, G. A. Cordell,), Elsevier, Evanston, Illinois, 2008, pp. 1-430
11. H.-J. Knölker, K. R. Reddy, Chem. Rev. 2002, 102, 4303-4427.
12. J. T. Kuethe, K. G. Childers, Adv. Synth. Catal. 2008, 350, 1577-1586
13. D. J. St. Jean, S. F. Poon, J. L. Schwarzbach, Org. Lett. 2007, 9, 4893-4896
14. T. Tsuchimoto, H. Matsubayashi, M. Kaneko, Y. Nagase, T. Miyamura, E. Shirakawa, J. Am. Chem. Soc. 2008, 130, 15823-15835
15. M. Yamashita, H. Horiguchi, K. Hirano, T. Satoh, M. Miura, J. Org. Chem. 2009, 74, 7481-7488
16. M. E. Budén, V. A. Vaillard, S. E. Martin, R. A. Rossi, J. Org. Chem. 2009, 74, 4490-4498
17. T. Tsuchimoto, H. Matsubayashi, M. Kaneko, E. Shirakawa, Y. Kawakami, Angew. Chem. 2005, 117, 1360-1364
18. Angew. Chem. Int. Ed. 2005, 44, 1336-1340
19. B. J. Stokes, B. Jovanovic, H. Dong, K. J. Richert, R. D. Riell, T. G. Driver, J. Org. Chem. 2009, 74, 3225-3228
20. J. K. Laha, P. Petrou, G. D. Cuny, J. Org. Chem. 2009, 74, 3152-3155
21. A. Kuwahara, K. Nakano, K. Nozaki, J. Org. Chem. 2005, 70, 413-419
22. M. Yamamoto, S. Matsubara, Chem. Lett. 2007, 36, 172-173
23. A. P. Antonchick, R. Samanta, K. Kulikov, J. Lategahn, Angew. Chem. 2011, 123, 8764-8767
24. Angew. Chem. Int. Ed. 2011, 50, 8605-8608. Selected recent dibenzofuran syntheses
25. K. Kawaguchi, K. Nakano, K. Nozaki, J. Org. Chem. 2007, 72, 5119-5128
26. J. Liu, A. E. Fitzgerald, N. S. Mani, J. Org. Chem. 2008, 73, 2951-2954
27. B. Liegault, D. Lee, M. P. Huestis, D. R. Stuart, K. Fagnou, J. Org. Chem. 2008, 73, 5022-5028
28. X. Guo, R. Yu, H. Li, Z. Li, J. Am. Chem. Soc. 2009, 131, 17387-17393
29. H. Xu, L.-L. Fan, Chem. Pharm. Bull. 2008, 56, 1496-1498
30. Z. Liu, R. C. Larock, Tetrahedron 2007, 63, 347-355.
31. W. C. P. Tsang, N. Zheng, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 14560-14561
32. W. C. P. Tsang, R. H. Munday, G. Brasche, N. Zheng, S. L. Buchwald, J. Org. Chem. 2008, 73, 7603-7610.
33. J. A. Jordan-Hore, C. C. C. Johansson, M. Gulias, E. M. Beck, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 16184-16186.
34. B.-J. Li, S.-L. Tian, Z. Fang, Z.-J. Shi, Angew. Chem. 2008, 120, 1131-1134
35. Angew. Chem. Int. Ed. 2008, 47, 1115-1118.
36. S. H. Cho, J. Yoon, S. Chang, J. Am. Chem. Soc. 2011, 133, 5996-6005.
37. B. Xiao, T.-J. Gong, Z.-J. Liu, J.-H. Liu, D.-F. Luo, J. Xu, L. Liu, J. Am. Chem. Soc. 2011, 133, 9250-9253.
38. D. E. Ames, A. Opalko, Synthesis 1983, 234-235
39. D. E. Ames, A. Opalko, Tetrahedron 1984, 40, 1919-1925
40. M. Parisien, D. Valette, K. Fagnou, J. Org. Chem. 2005, 70, 7578-7584
41. L.-C. Campeau, M. Parisien, A. Jean, K. Fagnou, J. Am. Chem. Soc. 2006, 128, 581-590
42. T. Iwaki, A. Yasuhara, T. Sakamoto, J. Chem. Soc. Perkin Trans. 1 1999, 1505-1510
43. R. B. Bedford, C. S. J. Cazin, Chem. Commun. 2002, 2310-2311
44. Z. Liu, R. C. Larock, Org. Lett. 2004, 6, 3739-3741
45. H.-J. Knölker, Curr. Org. Synth. 2004, 1, 309-331.
46. H.-J. Knölker, W. Frohner, J. Chem. Soc. Perkin Trans. 1 1998, 173-175
47. K. K. Gruner, H.-J. Knölker, Org. Biomol. Chem. 2008, 6, 3902-3904
48. R. Forke, A. Jager, H.-J. Knölker, Org. Biomol. Chem. 2008, 6, 2481-2483
49. R. Forke, M. P. Krahl, T. Krause, G. Schlechtingen, H.-J. Knölker, Synlett 2007, 2, 268-272
50. H.-J. Knölker, W. Frohner, K. R. Reddy, Synthesis 2002, 4, 557-564
51. H.-J. Knölker, N. O'Sullivan, Tetrahedron 1994, 50, 10893-10908
52. H.-J. Knölker, Chem. Lett. 2009, 38, 8-13
53. H.-J. Knölker, Top. Curr. Chem. 2005, 244, 115-148.
54. L. Ackermann, A. Althammer, Angew. Chem. 2007, 119, 1652-1654
55. Angew. Chem. Int. Ed. 2007, 46, 1627-1629
56. L. Ackermann, A. Althammer, P. Mayer, Synthesis 2009, 20, 3493-3503.
57. C. Wang, I. Piel, F. Glorius, J. Am. Chem. Soc. 2009, 131, 4194-4195.
58. C.Y. Liu, P. Knochel, Org. Lett. 2005, 7, 2543-2546.
59. C. Asche, M. Demeunynck, Anti-Cancer Agents Med. Chem. 2007, 7, 247-267
60. K. Thevissen, A. Marchand, P. Chaltin, E. M. K. Meert, B. P. A. Cammue, Curr. Med. Chem. 2009, 16, 2205-2211.
61. Y. Liu, M. Nishiura, Y. Wang, Z. Hou, J. Am. Chem. Soc. 2006, 128, 5592-5593
62. Y. Wu, Y. Li, S. Gardner, B. S. Ong, J. Am. Chem. Soc. 2005, 127, 614-618
63. S. Deechongkit, E. T. Powers, S. You, J. W. Kelly, J. Am. Chem. Soc. 2005, 127, 8562-8570
64. Z. Zhao, X. Xu, H. Wang, P. Lu, G. Yu, Y. Liu, J. Org. Chem. 2008, 73, 594-602.
65. M. Fagnoni, A. Albini, Acc. Chem. Res. 2005, 38, 713-721
66. S. Protti, M. Fagnoni, A. Albini, J. Am. Chem. Soc. 2006, 128, 10670-10671
67. V. Dichiarante, M. Fagnoni, Synlett 2008, 6, 787-800
68. A. Fraboni, M. Fagnoni, A. Albini, J. Org. Chem. 2003, 68, 4886-4893
69. V. Dichiarante, M. Fagnoni, A. Albini, Angew. Chem. 2007, 119, 6615-6618
70. Chem. Int. Ed. 2007, 46, 6495-6498
71. S. Milanesi, M. Fagnoni, A. Albini, Chem. Commun. 2003, 216-217
72. M. Mella, M. Fagnoni, A. Albini, Org. Biomol. Chem. 2004, 2, 3490-3495
73. V. Dichiarante, M. Fagnoni, M. Mella, A. Albini, Chem. Eur. J. 2006, 12, 3905-3915
74. Y. Apeloig, D. Arad, J. Am. Chem. Soc. 1985, 107, 5285-5286
75. C. G. Swain, J. E. Sheats, K. G. Harbison, J. Am. Chem. Soc. 1975, 97, 783-790
76. S. Lazzaroni, D. Dondi, M. Fagnoni, A. Albini, J. Org. Chem. 2008, 73, 206-211.
77. D. B. Kimball, M. M. Haley, Angew. Chem. 2002, 114, 3484-3498
78. Angew. Chem. Int. Ed. 2002, 41, 3338-3351
79. S. Bräse, Acc. Chem. Res. 2004, 37, 805-816
80. J. Zhou, J. He, B. Wang, W. Yang, H. Ren, J. Am. Chem. Soc. 2011, 133, 6868-6870
81. K. C. Nicolaou, C. N. C. Boddy, H. Li, A. E. Koumbis, R. Hughes, S. Natarajan, N. F. Jain, J. M. Ramanjulu, S. Bräse, M. E. Solomon, Chem. Eur. J. 1999, 5, 2602-2621
82. K. C. Nicolaou, C. N. C. Boddy, J. Am. Chem. Soc. 2002, 124, 10451-10455
83. C.-Y. Liu, P. Knochel, J. Org. Chem. 2007, 72, 7106-7115
84. S. Bräse, M. Schroen, Angew. Chem. 1999, 111, 1139-1142
85. Angew. Chem. Int. Ed. 1999, 38, 1071-1073
86. C. Gil, S. Bräse, J. Comb. Chem. 2009, 11, 175-197
87. M. Döbele, S. Vanderheiden, N. Jung, S. Bräse, Angew. Chem. 2010, 122, 6122-6125
88. Angew. Chem. Int. Ed. 2010, 49, 5986-5988
89. C.-Y. Liu, A. Gavryushin, P. Knochel, Chem. Asian J. 2007, 2, 1020-1030
90. N. Satyamurthy, J. R. Barrio, D. G. Schmidt, C. Kammerer, G. T. Bida, M. E. Phelps, J. Org. Chem. 1990, 55, 4560 4564.
91. in Metal-Catalyzed Cross-Coupling Reactions (Eds.:, F. Diederich, P. J. Stang,), Wiley-VCH, Weinheim, Germany, 1998
92. in Cross-Coupling Reactions. A Practical Guide (Ed.:, N. Miyaura,), Springer-Verlag, Berlin, 2002
93. in Metal-Catalyzed Cross-Coupling Reactions (Eds.:, A. de Meijere, F. Diederich,), Wiley-VCH, Weinheim, Germany, 2004.
94. T. Watanabe, S. Ueda, S. Inuki, S. Oishi, N. Fujii, H. Ohno, Chem. Commun. 2007, 4516-4518
95. M. P. Krahl, A. Jager, T. Krause, H.-J. Knolker, Org. Biomol. Chem. 2006, 4, 3215-3219.
96. T.-S. Wu, S.-C. Huang, P.-L. Wu, C.-S. Kuoh, Phytochemistry 1999, 52, 523-527
97. M. Fuchsenberger, R. Forke, H.-J. Knolker, Synlett 2011, 14, 2056-2058.
98. U. Songsiang, T. Thongthoom, C. Boonyarat, C. Yenjai, J. Nat. Prod. 2011, 74, 208-212.