A concise and diversity-oriented strategy for the synthesis of benzofurans and indoles via ugi and diels-alder reactions

Journal of Combinatorial Chemistry

Volumn 7, Issue 6, 2005, Pages 958-967

  Lu, Kui ^a,b,c   Luo, Tuoping ^a,b,c   Xiang, Zheng ^a,b,c   You, Zejin ^a,b,c   Fathi, Reza ^d   Chen, Jiahua ^a,b,c   Yang, Zhen ^a,b,c,d  

^a Peking University   (China)

^b PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^c PEKING UNIVERSITY   (China)

^d VivoQuest Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 28244470363     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc050099b     Document Type: Article

References (37)

1. (a) Donnelly, D. M. X.; Meegan, M. J. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Eds.; Pergamon Press: Oxford, 1984; Vol. 4, pp 657-712.
2. (b) Felder, C. C.; Joyce, K. E.; Briley, E. M.; et al. J. Pharmacol. Exp. Ther. 1998, 284, 291-297.
3. For a recent review, see: Toyota, M.; Ihara, M. Nat. Prod. Rep. 1998, 15, 327.
4. (a) Yasuzawa, T.; Muroi, K.; Ichimura M.; Takahashi, I.; Ogawa, T.; Takahashi, K.; Sano, H.; Saitoh, Y. Chem. Pharm. Bull. 1995, 43, 378.
5. (b) Salim, A. A.; Garson, M. J.; Craik, D. J. J. Nat. Prod. 2004, 67, 1719.
6. (c) Baell, J. B.; Gable, R. W.; Harvey, A. J.; Toovey, N.; Herzog, T.; Hänsel, W.; Wulff, H. J. Med. Chem. 2004, 47, 2326.
7. (d) Jiang, W.; Siu, Z.; Macielag, M. J.; Walsh, S. P.; Fiordeliso, J. J.; Lanter, J. C.; Guan, J.; Qiu, Y.; Kraft, P.; Bhattacharjee, S.; Craig, E.; Haynes-Johnson, D.; John, T. M.; Clancy, J. J. Med. Chem. 2003, 46, 441.
8. (a) Schreiber, S. L. Science 2000, 287, 1964.
9. (b) Nicolaou, K. C.; Pfefferkorn, J. A.; Cao, G.-Q.; Roecker, A. J.; Barluenga, S.; Mitchell, H. J. J. Am. Chem. Soc. 2000, 122, 9939.
10. (c) Park, W. K. C.; Auer, M.; Jaksche, H.; Wong, C.-H. J. Am. Chem. Soc. 1996, 118, 10150.
11. (d) Keating, T. A.; Armstrong, R. W. J. Am. Chem. Soc. 1995, 117, 7842.
12. (a) Hou, X.-L.; Yang, Z.; Wong, H. N. C. In Progress in Heterocyclic Chemistry; Gribble, G. W., Joule, J. A., Eds.; Pergamon: Oxford, 2003; pp 167-205.
13. (b) Janosik, T.; Bergman, J. in Progress in Heterocyclic Chemistry; Gribble, G. W., Joule, J. A., Eds.; Pergamon: Oxford, 2003; pp 140-166.
14. Tietze, L. F.; Haunert, F. In Stimulating Concepts in Chemistry; Shibasaki, M., Stoddart, J. F., Vögtle, F., Eds., Wiley-VCH: Weinheim, Germany, 2000; pp 39-64.
15. (a) Liao, Y.; Hu, Y.; Wu, J.; Zhu, Q.; Donovan, M.; Fathi, R.; Yang. Z. Curr. Med. Chem. 2003, 10, 2285.
16. (b) Xiang, Z.; Luo, T.; Lu, K.; Cui, J.; Shi, X.; Fathi, R.; Chen, J.; Yang, Z. Org. Lett. 2004, 6, 3155.
17. (a) Armstrong, R.; Combs, A.; Tempest, P.; Brown, D.; Keating, T. Acc. Chem. Res. 1996, 29, 123.
18. (b) Domling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168.
19. (b) Bienayme, H.; Hulme, C.; Oddon, G.; Schmidtt, P. Chem. - Eur. J. 2000, 6, 3321.
20. (1) Roush, W. R. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 5, pp 513-550.
21. Winkler, J. D. Chem. Rev. 1996, 96, 167.
22. (a) Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851.
23. (b) Zhang, J.; Jacobson, A.; Rusche, J. R.; Herlihy, W. J. Org. Chem. 1999, 64, 1074.
24. (c) Fayol, A.; Zhu, J. Angew. Chem., Int. Ed. 2002, 41, 3633.
25. (d) Wright, D. L.; Robotham, C. V.; Aboud, K. Tetrahedron Lett. 2002, 43, 943.
26. (e) Sello, J. K.; Andreana, P. R.; Lee, D.; Schreiber, S. L. Org. Lett. 2003, 5, 4125.
27. (f) Paulvannan, K. J. Org. Chem. 2004, 69, 1207.
28. (g) Oikawa, M.; Ikoma, M.; Sasaki, M. Tetrahedron Lett. 2005, 46, 415.
29. Burke, M. D.; Schreiber, S. L. Angew Chem. Int. Ed. 2004, 43, 46.
30. Krygowski, T. M.; Cyranski, M. K. Chem. Rev. 2001, 101, 1385.
31. Nakamichi, N.; Kawabata, H.; Hayashi, M. J. Org. Chem. 2003, 68, 8272.
32. (a) Bull, S. D.; Davies, S. G.; Fenton, G.; Mulvaney, A. W.; Prasad, R. S. Smith, A. D. J. Chem. Soc., Perkin Trans. 1 2000, 3765.
33. (b) Bull, S. D.; Davies, S. G.; Fenton, G.; Mulvaney, A. W.; Prasad, R. S.; Smith, A. D. J. Chem. Soc., Perkin Trans. 1 2000, 337.
34. (c) Chern, C.-Y.; Huang, Y.-P.; Kan, W. M. Tetrahedron Lett. 2003, 44, 1039.
35. (a) Clemons, P. A. Curr. Opin. Chem. Biol. 1999, 3, 112.
36. (b) Diver, S. T.; Schreiber, S. L. J. Am. Chem. Soc. 1997, 119, 5106 and related references therein,
37. (c) Nicolaou, K. C.; Hughes, R.; Cho, S.-Y.; Winssinger, N.; Smethurst, C.; Labischinski, H.; Endermann, R. Angew. Chem., Int. Ed. 2000, 39, 3823 and references therein.