Cu(OTf)2 catalysed [6+2] cycloaddition reaction for the synthesis of highly substituted pyrrolo[1,2-a]indoles: Rapid construction of the yuremamine core

Chemical Communications

Volumn 49, Issue 31, 2013, Pages 3260-3262

  Dethe, Dattatraya H ^a   Boda, Raghavender ^a   Das, Saikat ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; COPPER COMPLEX; INDOLE DERIVATIVE; PYRROLO[1,2 A]INDOLE DERIVATIVE; UNCLASSIFIED DRUG; YUREMAMINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CRYSTAL STRUCTURE; CYCLOADDITION; DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR OVERHAUSER EFFECT; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION OPTIMIZATION; STEREOCHEMISTRY;

EID: 84875458919     PISSN: 13597345     EISSN: 1364548X     Source Type: Journal    
DOI: 10.1039/c3cc40617b     Document Type: Article

References (35)

1. L. Hao, Y. Pan, T. Wang, M. Lin, L. Chen, Z.-P. Zhan, Adv. Synth. Catal., 2010, 352, 3215
2. R. Kakadiya, H. Dong, P.-C. Lee, N. Kapuriya, X. Zhang, T.-C. Chou, T.-C. Lee, K. Kapuriya, A. Shah, T.-L. Su, Bioorg. Med. Chem., 2009, 17, 5614
3. M. Tanaka, S. Sagawa, J.-I. Hoshi, F. Shimoma, K. Yasue, M. Ubukata, T. Ikemoto, Y. Hase, M. Takahashi, T. Sasase, N. Ueda, M. Matsushita, T. Inaba, Bioorg. Med. Chem., 2006, 14, 5781
4. U. Galm, M. H. Hager, S. G. V. Lanen, J. Ju, J. S. Thorson, B. Shen, Chem. Rev., 2005, 105, 739
5. W. A. Remers and R. T. Dorr, in Alkaloids: Chemical and Biological Perspectives, ed. S. W. Pelletier, John Wiley and Sons, New York, 1988, vol. 6, pp. 1-74
6. S. J. Danishefsky, J. M. Schkeryantz, Synlett, 1995, 475
7. L. S. Fernandez, M. F. Jobling, K. T. Andrews, V. M. Avery, Phytother. Res., 2008, 22, 1409
8. L. S. Fernandez, M. S. Buchanan, A. R. Carroll, Y. J. Feng, R. J. Quinn, V. M. Avery, Org. Lett., 2009, 11, 329
9. L. S. Fernandez, M. L. Sykes, K. T. Andrews, V. M. Avery, Int. J. Antimicrob. Agents, 2010, 36, 275
10. D. H. Dethe, R. D. Erande, A. Ranjan, J. Am. Chem. Soc., 2011, 133, 2864
11. R. M. Zeldin, F. D. Toste, Chem. Sci., 2011, 2, 1706
12. R. Vallakati, J. A. May, J. Am. Chem. Soc., 2012, 134, 6936
13. J.-F. Liu, Z.-Y. Jiang, R.-R. Wang, Y.-T. Zeng, J.-J. Chen, X.-M. Zhang, Y.-B. Ma, Org. Lett., 2007, 9, 4127
14. A. Karadeolian, M. A. Kerr, Angew. Chem., Int. Ed., 2010, 49, 1133
15. A. Karadeolian, M. A. Kerr, J. Org. Chem., 2010, 75, 6830
16. J. Lee, J. S. Panek, Org. Lett., 2011, 13, 502
17. X. Zhang, T. Mu, F. Zhan, L. Ma, G. Liang, Angew. Chem., Int. Ed., 2011, 50, 6164
18. W. Wu, M. Xiao, J. Wang, Y. Li, Z. Xie, Org. Lett., 2012, 14, 1624
19. C. V. Ramana, P. Patel, K. Vanka, B. Miao, A. Degterev, Eur. J. Org. Chem., 2010, 5955
20. P. Patel, C. V. Ramana, Org. Biomol. Chem., 2011, 9, 7327
21. C. V. Suneel Kumar, V. G. Puranik, C. V. Ramana, Chem.-Eur. J., 2012, 18, 9601
22. Q. Yin, S.-L. You, Chem. Sci., 2011, 2, 1344
23. J. J. Vepsalainen, S. Auriola, M. Tukiainen, N. Ropponen, J. C. Callaway, Planta Med., 2005, 71, 1053
24. R. D. R. S. Manian, J. Jayashankaran, R. Ragunathan, Synlett, 2007, 874
25. H. N. Borah, M. L. Deb, R. C. Boruah, P. J. Bhuyan, Tetrahedron Lett., 2005, 46, 3391
26. I. Yavari, M. Adib, M. H. Sayahi, J. Chem. Soc., Perkin Trans. 1, 2002, 1517
27. A. Padwa, G. E. Fryxell, J. R. Gasdaska, M. K. Venkatramanan, G. S. Wong, J. Org. Chem., 1989, 54, 644
28. K. Wood, D. S. Black, N. Kumar, Tetrahedron Lett., 2009, 50, 574
29. J. Takaya, Y. Miyashita, H. Kusama, N. Iwasawa, Tetrahedron, 2011, 67, 4455
30. M. B. Johansen, M. A. Kerr, Org. Lett., 2008, 10, 3497
31. D. V. Patil, M. A. Cavitt, S. France, Org. Lett., 2011, 13, 5820
32. K. Chen, Z. Zhang, Y. Wei, M. Shi, Chem. Commun., 2012, 48, 7696
33. H.-L. Cui, X. Feng, J. Peng, J. Lei, K. Jiang, Y.-C. Chen, Angew. Chem., Int. Ed., 2009, 48, 5737
34. W. B. Liu, X. Zhang, L. X. Dai, S. L. You, Angew. Chem., Int. Ed., 2012, 51, 5183
35. P. J. Das, J. Das, Tetrahedron Lett., 2012, 53, 4718