Synthesis of indene derivatives via electrophilic cyclization

Organic Letters

Volumn 11, Issue 1, 2009, Pages 229-231

  Khan, Zulfiqar Ali ^a   Wirth, Thomas ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

INDENE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

CYCLIZATION; INDENES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 59649093541     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8024956     Document Type: Article

References (43)

1. (a) Hagishita, S.; Yamada, M.; Shirahase, K.; Okada, T.; Murakami, Y.; Ito, Y.; Matsuura, T.; Wada, M.; Kato, T. J. Med. Chem. 1996, 39, 3636.
2. (b) Palm, J.; Boegesoe, K. P.; Liljefors, T. J. Med. Chem. 1993, 36, 2878.
3. (c) Clegg, N. J.; Paruthiyil, S.; Leitman, D. C.; Scanlan, T. S. J. Med. Chem. 2005, 48, 5989-6003.
4. (d) Witiak, D. T.; Kakodkar, S. V.; Brunst, G. E.; Baldwin, J. R.; Rahwan, R. G. J. Med. Chem. 1978, 21, 1313.
5. (e) Gao, H.; Katzenellenbogen, J. A.; Garg, R.; Hansch, C. Chem. ReV. 1999, 99, 723.
6. Alt, H. G.; Koeppl, A. Chem. Rev. 2000, 100, 1205.
7. Prough, J. D.; Alberts, A. W.; Deana, A. A.; Gilfillian, J. L.; Huff, J. W.; Smith, R. L.; Wiggins, J. M. J. Med. Chem. 1990, 33, 758.
8. Sun, X.; Izumi, K.-J.; Hu, C.-Q.; Lin, G.-Q. Chin. J. Chem. 2006, 24, 430.
9. Yoshida, H.; Kato, M.; Ogata, T. J. Org. Chem. 1985, 50, 1145.
10. (a) Quan, L. G.; Gevorgyan, V.; Yamamoto, Y. J. Am. Chem. Soc. 1999, 121, 3545.
11. (b) Gevorgyan, V.; Quan, L. G.; Yamamoto, Y. Tetrahedron Lett. 1999, 40, 4089.
12. (c) Zhang, D.; Liu, Z.; Yum, E. K.; Larock, R. C. J. Org. Chem. 2007, 72, 251.
13. (d) Zhang, D.; Yum, E. K.; Liu, Z.; Larock, R. C. Org. Lett. 2005, 7, 4963.
14. (e) Bi, H.-P.; Liu, X.-Y.; Gou, F.-R.; Guo, L.-N.; Duan, X.-H.; Liang, Y.-M. Org. Lett. 2007, 9, 3527.
15. (a) Deng, R.; Sun, L.; Li, Z. Org. Lett. 2007, 9, 5207.
16. (b) Rayabarapu, D. K.; Cheng, C.-H. Chem. Commun. 2002, 942.
17. (c) Rayabarapu, D. K.; Yang, C.-H.; Cheng, C.-H. J. Org. Chem. 2003, 68, 6726.
18. (a) Chang, K.-J.; Rayabarapu, D. K.; Cheng, C.-H. Org. Lett. 2003, 5, 3963.
19. (b) Chang, K.-J.; Rayabarapu, D. K.; Cheng, C.-H. J. Org. Chem. 2004, 69, 4781.
20. Tutar, A.; Cakmak, O.; Balci, M. Tetrahedron 2001, 57, 9759.
21. Saito, S.; Homma, M.; Gevorgyan, V.; Yamamoto, Y. Chem. Lett. 2000, 722.
22. Roussel, C.; Rajoharison, H. G.; Bizzari, L.; Shaimi, L. J. Org. Chem. 1988, 53, 683.
23. Moss, R. A.; Xue, S.; Sauers, R. R. J. Am. Chem. Soc. 1996, 118, 10307.
24. Zhou, X.; Zhang, H.; Xie, X.; Li, Y. J. Org. Chem. 2008, 73, 3958.
25. French, A. N.; Bissmire, S.; Wirth, T. Chem. Soc. Rev. 2004, 33, 354.
26. Bi, H.-P.; Guo, L.-N.; Duan, X.-H.; Gou, F.-R.; Huang, S.-H.; Liu, X.-Y.; Liang, Y. M. Org. Lett. 2007, 9, 397.
27. Barluenga, J.; Palomas, D.; Rubio, E.; Gonzalez, J. M. Org. Lett. 2007, 9, 2823.
28. (a) Kitagawa, O.; Inoue, T.; Hirano, K.; Taguchi, T. J. Org. Chem. 1993, 58, 3106.
29. (b) Kitagawa, O.; Taguchi, T. Synlett., 1999, 1191.
30. (a) Knight, D. W. Prog. Heterocycl. Chem. 2002, 14, 19.
31. (b) Zhang, L.; Kozmin, S. A. J. Am. Chem. Soc. 2005, 125, 6962.
32. (c) Foot, O. F.; Knight, D. W.; Low, A. C. L.; Li, Y. Tetrahedron Lett. 2007, 48, 647.
33. Larock, R. C.; Fried, C. A. J. Am. Chem. Soc. 1990, 112, 5882.
34. CCDC 705766 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc-.cam.ac.uk/conts/ retrieving.html (or from the CCDC, 12 Union Road, Cambridge CB2 1EZ, UK.; fax: +44 1223 336033; e-mail: deposit@ ccdc.cam.ac.uk).
35. (a) Montoro, R.; Wirth, T. Org. Lett. 2003, 5, 4729.
36. (b) Montoro, R.; Wirth, T. Synthesis 2005, 1473.
37. (c) Minakata, S.; Morino, Y.; Ide, T.; Oderaotoshi, Y.; Komatsu, M. Chem. Commun. 2007, 3279.
38. Beckwith, A. L. J.; Tozer, M. J. Tetrahedron Lett. 1992, 33, 4975.
39. Curran, D. P.; Chen, M.-H.; Spletzer, E.; Seong, C. M.; Chang, C.-T. J. Am. Chem. Soc. 1989, 111, 8872.
40. (a) Richardson, R. D.; Wirth, T. Angew. Chem., Int. Ed. 2006, 45, 4402.
41. (b) Richardson, R. D.; Page, T. K.; Altermann, S. M.; Paradine, S. M.; French, A. N.; Wirth, T. Synlett., 2007, 538.
42. (c) Ochiai, M.; Miyamoto, K. Eur. J. Org. Chem. 2008, 4229.
43. (d) Altermann, S. M.; Richardson, R. D.; Page, T. K.; Schmidt, R. K.; Holland, E.; Mohammed, U.; Paradine, S. M.; French, A. N.; Richter, C.; Bahar, A. M.; Witulski, B.; Wirth, T. Eur. J. Org. Chem. 2008, 5315.