Tandem cyclopropane ring-opening/conia-ene reactions of 2-alkynyl indoles: A [3 + 3] annulative route to tetrahydrocarbazoles

Organic Letters

Volumn 13, Issue 2, 2011, Pages 220-223

  Grover, Huck K ^a   Lebold, Terry P ^a   Kerr, Michael A ^a  

^a UNIVERSITY OF WESTERN ONTARIO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 78651488753     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102627e     Document Type: Article

References (66)

1. For reviews on the synthesis and functionalization of indoles, see
2. Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608
3. Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875
4. Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873
5. Sundberg, R. J. Indoles; Academic: New York, 1996.
6. Knölker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303
7. Clausamines: Ito, C.; Katsuno, S.; Ruangrungsi, N.; Furukawa, H. Chem. Pharm. Bull. 1998, 46, 344
8. Staurosporine: Satoshi, O.; Yuzuru, I.; Atushi, H.; Akira, N.; Juichi, A.; Hisae, T.; Yoko, T.; Rokurou, M. J. Antibiot. 1977, 30, 275
9. Aflavazole: TePaske, M. R.; Gloer, J. B.; Wicklow, D. T.; Dowd, P. F. J. Org. Chem. 1990, 55, 5299
10. Lebold, T. P.; Kerr, M. A. Org. Lett. 2008, 10, 997
11. Lebold, T. P.; Kerr, M. A. Org. Lett. 2007, 9, 1883
12. Lebold, T. P.; Leduc, A. B.; Kerr, M. A. Org. Lett. 2009, 11, 3770
13. Leduc, A. B.; Lebold, T. P.; Kerr, M. A. J. Org. Chem. 2009, 74, 8414
14. For reviews on donor-acceptor cyclopropanes, see
15. Carson, C. A.; Kerr, M. A. Chem. Soc. Rev. 2009, 38, 3051
16. Rubin, M.; Rubina, M.; Gevorgyan, V. Chem. Rev. 2007, 107, 3117
17. Yu, M.; Pagenkopf, B. L. Tetrahedron 2005, 61, 321
18. Reissig, H.-U.; Zimmer, R. Chem. Rev. 2003, 103, 1151
19. Wong, H. N. C.; Hon, M.-Y.; Tse, C.-W.; Yip, Y.-C.; Tanko, J.; Hudlicky, T. Chem. Rev. 1989, 89, 165
20. Danishefsky, S. Acc. Chem. Res. 1979, 12, 66
21. For leading references on the synthesis of heterocycles from cyclopropanes, see
22. Jackson, S. K.; Karadeolian, A.; Driega, A. B.; Kerr, M. A. J. Am. Chem. Soc. 2008, 130, 4196
23. Carson, C. A.; Kerr, M. A. J. Org. Chem. 2005, 70, 8242
24. Young, I. S.; Kerr, M. A. Angew. Chem., Int. Ed. 2003, 42, 3023
25. Pohlhaus, P. D.; Johnson, J. S. J. Am. Chem. Soc. 2005, 127, 16014
26. Korotkov, V. S.; Larionov, O. V.; Hofmeister, A.; Magull, J.; de Meijere, A. J. Org. Chem. 2007, 72, 7504
27. Pohlhaus, P. D.; Sanders, S. D.; Parsons, A. T.; Li, W.; Johnson, J. S. J. Am. Chem. Soc. 2008, 130, 8642
28. Perreault, C.; Goudreau, S. R.; Zimmer, L. E.; Charette, A. B. Org. Lett. 2008, 10, 689
29. Ivanova, O. A.; Budynina, E. M.; Grishin, Y. K.; Trushkov, I. V.; Verteletskii, P. V. Angew. Chem., Int. Ed. 2008, 47, 1107
30. Lebold, T. P.; Kerr, M. A. Org. Lett. 2009, 11, 4354
31. Thermal: Conia, J. M.; Le Perchec, P. Synthesis 1975, 1
32. Au mediated
33. Pan, J.-H.; Yang, M.; Gao, Q.; Zhu, N.-Y.; Yang, D. Synthesis 2007, 2539
34. Ochida, A.; Ito, H.; Sawamura, M. J. Am. Chem. Soc. 2006, 128, 16486
35. Staben, S. T.; Kennedy-Smith, J. J.; Toste, F. D. Angew. Chem., Int. Ed. 2004, 43, 5350
36. Kennedy-Smith, J. J.; Staben, S. T.; Toste, F. D. J. Am. Chem. Soc. 2004, 126, 4526
37. Pd mediated
38. Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc. 2007, 129, 2764
39. Corkey, B. K.; Toste, F. D. J. Am. Chem. Soc. 2005, 127, 17168
40. In mediated
41. Hatakeyama, S. Pure Appl. Chem. 2009, 81, 217
42. Itoh, Y.; Tsuji, H.; Yamagata, K.-i.; Endo, K.; Tanaka, I.; Nakamura, M.; Nakamura, E. J. Am. Chem. Soc. 2008, 130, 17161
43. Takahashi, K.; Midori, M.; Kawano, K.; Ishihara, J.; Hatakeyama, S. Angew. Chem., Int. Ed. 2008, 47, 6244
44. Tsuji, H.; Yamagata, K.-i.; Itoh, Y.; Endo, K.; Nakamura, M.; Nakamura, E. Angew. Chem., Int. Ed. 2007, 46, 8060
45. Cu/Ag cocatalyzed
46. Deng, C.-L.; Zou, T.; Wang, Z.-Q.; Song, R.-J.; Li, J.-H. J. Org. Chem. 2009, 74, 412
47. Deng, C.-L.; Song, R.-J.; Guo, S.-M.; Wang, Z.-Q.; Li, J.-H. Org. Lett. 2007, 9, 5111
48. Ni mediated
49. Gao, Q.; Zheng, B.-F.; Li, J.-H.; Yang, D. Org. Lett. 2005, 7, 2185
50. Ti mediated
51. Kitigawa, O.; Suzuki, T.; Inoue, T.; Watanabe, Y.; Taguchi, T. J. Org. Chem. 1998, 63, 9470
52. Co mediated
53. Renaud, J.-L.; Aubert, C.; Malacria, M. Tetrahedron 1999, 55, 5113
54. Cruciani, P.; Stammler, R.; Aubert, C.; Malacria, M. J. Org. Chem. 1996, 61, 2699
55. Cruciani, P.; Aubert, C.; Malacria, M. Tetrahedron Lett. 1994, 35, 6677
56. Zn mediated
57. Morikawa, S.; Yamazaki, S.; Tsukada, M.; Izuhara, S.; Morimoto, T.; Kakiuchi, K. J. Org. Chem. 2007, 72, 6459
58. Morikawa, S.; Yamazaki, S.; Furusaki, Y.; Amano, N.; Zenke, K.; Kakiuchi, K. J. Org. Chem. 2006, 71, 3540
59. Nakamura, M.; Liang, C.; Nakamura, E. Org. Lett. 2004, 6, 2015
60. Cavicchioli, M.; Marat, X.; Monteiro, N.; Hartmann, B.; Balme, G. Tetrahedron Lett. 2002, 43, 2609
61. Marat, X.; Monteiro, N.; Balme, G. Synlett 1997, 845
62. Cu mediated
63. Montel, S.; Bouyssi, D.; Balme, G. Adv. Synth. Catal. 2010, 352, 2315
64. Harrington, P. E.; Kerr, M. A. Tetrahedron Lett. 1997, 38, 5949
65. Kerr, M. A.; Keddy, R. G. Tetraheron Lett. 1999, 5671
66. England, D. B.; Kuss, T. D. O.; Keddy, R. G.; Kerr, M. A. J. Org. Chem. 2001, 66, 4704