Synthesis of Tryptanthrins by Organocatalytic and Substrate Co-catalyzed Photochemical Condensation of Indoles and Anthranilic Acids with Visible Light and O2

Organic Letters

Volumn 18, Issue 21, 2016, Pages 5744-5747

  Li, Xiangmin ^a   Huang, He ^b   Yu, Chenguang ^b   Zhang, Yueteng ^b   Li, Hao ^a   Wang, Wei ^a,b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b UNIVERSITY OF NEW MEXICO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84994663254     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/acs.orglett.6b03009     Document Type: Article

References (45)

1. Kshirsagar, U. A. Org. Biomol. Chem. 2015, 13, 9336 10.1039/C5OB01379H
2. Bergman, J. Phytochemistry 1989, 28, 3547 10.1016/0031-9422(89)80390-5
3. Bhattacharjee, A. K.; Skanchy, D. J.; Jennings, B.; Hudson, T. H.; Brendle, J. J.; Werbovetz, K. A. Bioorg. Med. Chem. 2002, 10, 1979 10.1016/S0968-0896(02)00013-5
4. Jao, C. W.; Lin, W. C.; Wu, Y. T.; Wu, P. L. J. Nat. Prod. 2008, 71, 1275 10.1021/np800064w
5. Chen, M.; Gan, L.; Lin, S.; Wang, X.; Li, L.; Li, Y.; Zhu, C.; Wang, Y.; Jiang, B.; Jiang, J.; Yang, Y.; Shi, J. J. Nat. Prod. 2012, 75, 1167 10.1021/np3002833
6. Honda, G.; Tabata, M.; Tsuda, M. Planta Med. 1979, 37, 172 10.1055/s-0028-1097320
7. Bandekar, P. P.; Roopnarine, K. A.; Parekh, V. J.; Mitchell, T. R.; Novak, M. J.; Sinden, R. P. J. Med. Chem. 2010, 53, 3558 10.1021/jm901847f
8. Kawakami, J.; Matsushima, N.; Ogawa, Y.; Kakinami, H.; Nakane, A.; Kitahara, H.; Nagaki, M.; Ito, S. Trans. Mater. Res. Soc. Jpn. 2011, 36, 603 10.14723/tmrsj.36.603
9. Honda, G.; Tabata, M. Planta Med. 1979, 36, 85 10.1055/s-0028-1097245
10. Bhattacharjee, A. K.; Skanchy, D. J.; Jennings, B.; Hudson, T. H.; Brendle, J. J.; Werbovetz, K. A. Bioorg. Med. Chem. 2002, 10, 1979 10.1016/S0968-0896(02)00013-5
11. Hwang, J.-M.; Oh, T.; Kaneko, T.; Upton, A. M.; Franzblau, S. G.; Ma, Z.; Cho, S.-N.; Kim, P. J. Nat. Prod. 2013, 76, 354 10.1021/np3007167
12. Bhattacharjee, A. K.; Hartell, M. G.; Nichols, D. A.; Hicks, R. P.; Stanton, B.; van Hamont, J. E.; Milhous, W. K. Eur. J. Med. Chem. 2004, 39, 59 10.1016/j.ejmech.2003.10.004
13. Chan, H. L.; Yip, H. Y.; Mak, N. K.; Leung, K. N. Cell. Mol. Immunol. 2009, 6, 335 10.1038/cmi.2009.44
14. Miao, S.; Shi, X.; Zhang, H.; Wang, S.; Sun, J.; Hua, W.; Miao, Q.; Zhao, Y.; Zhang, C. Int. J. Mol. Sci. 2011, 12, 3831 10.3390/ijms12063831
15. Yang, S.; Li, X.; Hu, F.; Li, Y.; Yang, Y.; Yan, J.; Kuang, C.; Yang, Q. J. Med. Chem. 2013, 56, 8321 10.1021/jm401195n
16. Tucker, A. M.; Grundt, P. ARKIVOC 2012, 546
17. Moskovkina, T. V.; Kalinovskii, A. I.; Makhan'kov, V. V. Russ. J. Org. Chem. 2012, 48, 123 10.1134/S1070428012010204
18. Batanero, B.; Barba, F. Tetrahedron Lett. 2006, 47, 8201 10.1016/j.tetlet.2006.09.130
19. Abe, T.; Itoh, T.; Choshi, T.; Hibino, S.; Ishikura, M. Tetrahedron Lett. 2014, 55, 5268 10.1016/j.tetlet.2014.07.113
20. Gahtory, D.; Chouhan, M.; Sharma, R.; Nair, V. A. Org. Lett. 2013, 15, 3942 10.1021/ol401709t
21. Jia, F.-C.; Zhou, Z.-W.; Xu, C.; Wu, Y.-D.; Wu, A.-X. Org. Lett. 2016, 18, 2942 10.1021/acs.orglett.6b01291
22. Bergman, J.; Egestad, B.; Lindstroem, J. O. Tetrahedron Lett. 1977, 18, 2625 10.1016/S0040-4039(01)83838-7
23. Yu, S. T.; Chern, J. W.; Chen, T. M.; Chiu, Y. F.; Chen, H. T.; Chen, Y. H. Acta Pharmacol. Sin. 2010, 31, 259 10.1038/aps.2009.198
24. Kumar, A.; Tripathi, V. D.; Kumar, P. Green Chem. 2011, 13, 51 10.1039/C0GC00523A
25. Jahng, K. C.; Kim, S. I.; Kim, D. H.; Seo, C. S.; Son, J. K.; Lee, S. H.; Lee, E. S.; Jahng, Y. D. Chem. Pharm. Bull. 2008, 56, 607 10.1248/cpb.56.607
26. Bergman, J.; Lindstroem, J. O.; Tilstam, U. Tetrahedron 1985, 41, 2879 10.1016/S0040-4020(01)96609-8
27. Eguchi, S.; Takeuchi, H.; Matsushita, Y. Heterocycles 1992, 33, 153 10.3987/COM-91-S62
28. Wang, C.; Zhang, L.; Ren, A.; Lu, P.; Wang, Y. Org. Lett. 2013, 15, 2982 10.1021/ol401144m
29. Lygin, A. V.; de Meijere, A. Org. Lett. 2009, 11, 389 10.1021/ol802659m
30. Vaidya, S. D.; Argade, N. P. Org. Lett. 2013, 15, 4006 10.1021/ol4018062
31. Cai, Z. J.; Wang, S. Y.; Ji, S. J. Org. Lett. 2013, 15, 5226 10.1021/ol4023936
32. Abe, T.; Itoh, T.; Choshi, T.; Hibino, S.; Ishikura, M. Tetrahedron Lett. 2014, 55, 5268 10.1016/j.tetlet.2014.07.113
33. Nelson, A. C.; Kalinowski, E. S.; Jacobson, T. L.; Grundt, P. Tetrahedron Lett. 2013, 54, 6804 10.1016/j.tetlet.2013.09.124
34. Yoon, T. P.; Ischay, M. A.; Du, J. Nat. Chem. 2010, 2, 527 10.1038/nchem.687
35. Narayanam, J. M. R.; Stephenson, C. R. J. Chem. Soc. Rev. 2011, 40, 102 10.1039/B913880N
36. Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322 10.1021/cr300503r
37. Schultz, D. M.; Yoon, T. P. Science 2014, 343, 1239176 10.1126/science.1239176
38. Nicewicz, D. A.; Nguyen, T. M. ACS Catal. 2014, 4, 355 10.1021/cs400956a
39. Xuan, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 6828 10.1002/anie.201200223
40. Zou, Y.; Lu, L.; Fu, L.; Chang, N.; Rong, J.; Chen, J.; Xiao, W.-J. Angew. Chem., Int. Ed. 2011, 50, 7171 10.1002/anie.201102306
41. Zou, Y.; Chen, J.; Liu, X.; Lu, L.; Davis, R. L.; Jørgensen, K. A.; Xiao, W.-J. Angew. Chem., Int. Ed. 2012, 51, 784 10.1002/anie.201107028
42. Li, X.; Gu, X.; Li, Y.; Li, P. ACS Catal. 2014, 4, 1897 10.1021/cs5005129
43. Lima, C. G. S.; de M. Lima, T.; Duarte, M.; Jurberg, I. D.; Paixão, M. W. ACS Catal. 2016, 6, 1389 10.1021/acscatal.5b02386
44. Babu, D. D.; Su, R.; El-Shafei, A.; Adhikari, A. V. Electrochim. Acta 2016, 198, 10 10.1016/j.electacta.2016.03.061
45. Ling, K.-Q.; Sayre, L. M. Bioorg. Med. Chem. 2005, 13, 3543 10.1016/j.bmc.2005.02.013