A novel lewis acid catalyzed [3 + 3]-annulation strategy for the syntheses of tetrahydro-β-carbolines and tetrahydroisoquinolines

Organic Letters

Volumn 15, Issue 11, 2013, Pages 2628-2631

  Wang, Shaoyin ^a,b   Chai, Zhuo ^a   Zhou, Shuangliu ^a   Wang, Shaowu ^a   Zhu, Xiancui ^a   Wei, Yun ^a  

^a ANHUI NORMAL UNIVERSITY   (China)

^b WANNAN MEDICAL COLLEGE   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84879211490     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol4008525     Document Type: Article

References (45)

1. Cao, R.; Peng, W.; Wang, Z.; Xu, A. Curr. Med. Chem. 2007, 14, 479
2. O'Connor, S. E.; Maresh, J. J. Nat. Prod. Rep. 2006, 23, 532
3. El-Sayed, M.; Verpoorte, R. Phytochem. Rev. 2007, 6, 277
4. Chen, F. E.; Huang, J. Chem. Rev. 2005, 105, 4671
5. Bentley, K. W. Nat. Prod. Rep. 2006, 23, 444
6. Jack, D.; Williams, R. Chem. Rev. 2002, 102, 1669
7. Phillipson, J. D.; Roberts, M. F.; Zenk, M. H., Eds. The Chemistry and Biology of Isoquinoline Alkaloids; Springer: Berlin, 1985.
8. Stöckkigt, J.; Antonchick, A. P.; Wu, F.; Waldmann, H. Angew. Chem., Int. Ed. 2011, 50, 8538
9. You, S.-L.; Cai, Q.; Zeng, M. Chem. Soc. Rev. 2009, 38, 2190
10. Lorenz, M.; VanLinn, M. L.; Cook, J. M. Curr. Org. Synth. 2010, 7, 189
11. Chrzanowska, M.; Rozwadowska, M. Chem. Rev. 2004, 104, 3341
12. Ascic, E.; Jensen, J. L.; Nielsen, T. E. Angew. Chem., Int. Ed. 2011, 50, 5188
13. Cai, Q.; Liang, X.-W.; Wang, S.-G.; Zhang, J.-W.; Zhang, X.; You, S.-L. Org. Lett. 2012, 14, 5022
14. Muratore, M. E.; Holloway, C. A.; Pilling, A. W.; Storer, R. I.; Trevitt, G.; Dixon, D. J. J. Am. Chem. Soc. 2009, 131, 10796
15. Huang, D.; Xu, F.; Lin, X.; Wang, Y. Chem.-Eur. J. 2012, 18, 3148
16. Wanner, M. J.; van der Haas, R. N. S.; de Cuba, K. R.; van Maarseveen, J. H.; Hiemstra, H. Angew. Chem., Int. Ed. 2007, 46, 7485
17. Seayad, J.; Seayad, A. M.; List, B. J. Am. Chem. Soc. 2006, 128, 1086
18. Raheem, I. T.; Thiara, P. S.; Peterson, E. A.; Jacobsen, E. N. J. Am. Chem. Soc. 2007, 129, 13404
19. Taylor, M. S.; Jacobsen, E. N. J. Am. Chem. Soc. 2004, 126, 10558
20. Li, C.-J. Acc. Chem. Res. 2009, 42, 335
21. Campos, K. R. Chem. Soc. Rev. 2007, 36, 1069
22. Jones, K. M.; Karier, P.; Klussmann, M. ChemCatChem 2012, 4, 51
23. Zhang, G.; Ma, Y.; Wang, S.; Kong, W.; Wang, R. Chem. Sci. 2013, 4, doi: 10.1039/C3S C50604E.
24. Berhal, F.; Wu, Z.; Zhang, Z.; Ayad, T.; Ratovelomanana-Vidal, V. Org. Lett. 2012, 14, 3308
25. Xie, J.-H.; Yan, P.-C.; Zhang, Q.-Q.; Yuan, K. X.; Zhou, Q.-L. ACS Catal. 2012, 2, 561
26. Chang, M.; Li, W.; Zhang, X. Angew. Chem., Int. Ed. 2011, 50, 10679
27. Li, C.; Xiao, J. J. Am. Chem. Soc. 2008, 130, 13208
28. Xu, Q.-L.; Dai, L.-X.; You, S.-L. Org. Lett. 2012, 14, 2579
29. Richter-Addo, G. B.; Knight, D. A.; Dewey, M. A.; Arit, A. M.; Gladyz, J. A. J. Am. Chem. Soc. 1993, 115, 11863 and ref 2d
30. Kobayashi, S.; Sugiura, M.; Kitagawa, H.; Lam, W. W.-L. Chem. Rev. 2002, 102, 2227
31. Prakash, G. K. S.; Mathew, T.; Olah, G. A. Acc. Chem. Res. 2011, 45, 565
32. Luo, S.; Zhu, L.; Talukdar, A.; Zhang, G.; Mi, X.; Cheng, J.-P.; Wang, P. G. Mini-Rev. Org. Chem. 2005, 2, 177
33. Noji, M.; Konno, Y.; Ishii, K. J. Org. Chem. 2007, 72, 5161
34. Noji, M.; Ohno, T.; Fuji, K.; FuIshii, K. J. Org. Chem. 2003, 68, 9340
35. Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S. Synlett 1996, 557
36. Tsuchimoto, T.; Tobita, K.; Hiyama, T.; Fukuzawa, S. J. Org. Chem. 1997, 62, 6997
37. Sharma, G. V. M; Mahalingam, A. K. J. Org. Chem. 1999, 64, 8943
38. Stankovic, S.; D'Hooghe, M.; Catak, S.; Eum, H.; Waroquier, M.; Van Speybroeck, V.; De Kimpe, N.; Ha, H.-J. Chem. Soc. Rev. 2012, 41, 643
39. Singh, G. S.; D'Hooghe, M.; De Kimpe, N. Chem. Rev. 2007, 107, 2080
40. Lu, P. Tetrahedron 2010, 66, 2549
41. Waller, F. J.; Barrett, A. G. M.; Braddock, D. C.; McKinnell, R. M.; Ramprasad, D. J. Chem. Soc., Perkin Trans. 1 1999, 867
42. Tsuruta, H.; Yamaguchi, K.; Imamoto, T. Chem. Commun. 1999, 1703
43. CCDC 924751 (3a), 924752 (3k), 924753 (5l), 924754 (5p), and 930713 (7) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data -request/cif.
44. Ghorai, M. K.; Shukla, D.; Bhattach- aryya, A. J. Org. Chem. 2012, 77, 3740
45. Ghorai, M. K.; Das, K.; Shukla, D. J. Org. Chem. 2007, 72, 5859 and ref 7b