Total synthesis and cytotoxicity of bisebromoamide and its analogues

Tetrahedron Letters

Volumn 52, Issue 17, 2011, Pages 2124-2127

  Li, Wenhua ^a   Yu, Shouyun ^a   Jin, Mingzhi ^a   Xia, Hongguang ^a   Ma, Dawei ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; BISEBROMOAMIDE; UNCLASSIFIED DRUG;

ARTICLE; CELL PROLIFERATION; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HELA CELL; HUMAN; HUMAN CELL; STEREOISOMERISM;

EID: 79953197887     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.058     Document Type: Article

References (31)

1. Teruya, T.; Sasaki, H.; Fukazawa, H.; Suenaga, K. Org. Lett. 2009, 11, 5062.
2. (a) Jansen, R.; Kunze, B.; Reichenback, H.; Jurkiewicz, E.; Hunsmann, G.; Hofle, G. Liebigs Ann. Chem. 1992, 357;
3. (b) Jansen, R.; Schomburg, D.; Hofle, G. Liebigs Ann. Chem. 1993, 701.
4. (a) Randazzo, A.; Bifulco, G.; Giannini, C.; Bucci, M.; Debitus, C.; Cirino, G.; Gomez-Paloma, L. J. Am. Chem. Soc. 2001, 123, 10870;
5. (b) Monica, C. D.; Randazzo, A.; Bifulco, G.; Cimino, P.; Aquino, M.; Izzo, I.; De Riccardis, F.; Gomez-Paloma, L. Tetrahedron Lett. 2002, 43, 5707;
6. (c) Nicolaou, K. C.; Schlawe, D.; Kim, D. W.; Longbottom, D. A.; de Noronha, R. G.; Lizos, D. E.; Manam, R. R.; Faulkner, D. J. Chem. Eur. J. 2005, 11, 6197.
7. Kanchan, T.; Paul, V. J.; Luesch, H. J. Am. Chem. Soc. 2008, 130, 1806.
8. For our recent studies on the synthesis of cyclodepsipeptides, see: (a) Yu, S.; Pan, X.; Lin, X.; Ma, D. Angew. Chem., Int. Ed. 2005, 44, 135;
9. (b) Xie, W.; Zou, B.; Pei, D.; Ma, D. Org. Lett. 2005, 7, 2775;
10. (c) Zou, B.; Long, K.; Ma, D. Org. Lett. 2005, 7, 4237;
11. (d) Yu, S.; Pan, X.; Ma, D. Chem. Eur. J. 2006, 12, 6572;
12. (e) Ma, D.; Zou, B.; Cai, G.; Hu, X.; Liu, J. O. Chem. Eur. J. 2006, 12, 7615;
13. (f) Xie, W.; Ding, D.; Zi, W.; Li, G.; Ma, D. Angew. Chem., Int. Ed. 2008, 47, 2844;
14. (g) Tan, L.; Ma, D. Angew. Chem., Int. Ed. 2008, 47, 3614;
15. (h) Li, W.; Gan, J.; Ma, D. Angew. Chem., Int. Ed. 2009, 48, 8891;
16. (i) Li, W.; Gan, J.; Ma, D. Org. Lett. 2009, 11, 5694;
17. (j) Li, W.; Schlecker, A.; Ma, D. Chem. Commun. 2010, 5403.
18. Gao, X.; Liu, Y.; Kwong, S.; Xu, Z.; Ye, T. Org. Lett. 2010, 12, 3018.
19. (a) Wipf, P.; Fritch, P. C. J. Am. Chem. Soc. 1996, 118, 12358;
20. (b) Wipf, P.; Fritch, P. C.; Geib, S. J.; Sefler, A. M. J. Am. Chem. Soc. 1998, 120, 4105;
21. (c) McKeever, B.; Pattenden, G. Tetrahedron 2003, 59, 2713. And see also Refs. 5a,d.
22. Deguest, G.; Bischoff, L.; Fruit, C.; Marsais, F. Tetrahedron: Asymmetry 2006, 17, 2120.
23. Charier, J.-D.; Duffy, J. E. S.; Hitchcock, P. B.; Young, D. W. J. Chem. Soc., Perkin Trans. 1 2001, 2367.
24. Zlatopolskiy, B. D.; Loscha, K.; Alvermann, P.; Kozhushkov, S. I.; Nikolaev, S. V.; Zeeck, A.; de Meijere, A. Chem. Eur. J. 2004, 10, 4708.
25. Deiters, A.; Chen, K.; Eary, C. T.; Martin, S. F. J. Am. Chem. Soc. 2003, 125, 4541.
26. Conrow, R.; Portoghese, P. S. J. Org. Chem. 1986, 51, 938.
27. (a) Seebach, V. D.; Aebi, J. D.; Gander-Coquoz, M.; Naef, R. Helv. Chim. Acta 1987, 70, 1194;
28. (b) Pattenden, G.; Thom, S. M.; Jones, M. F. Tetrahedron 1993, 49, 2131;
29. (c) Boyce, R. J.; Mulqueen, G. C.; Pattenden, G. Tetrahedron 1995, 51, 7321.
30. (a) Bergeron, R. J.; Wiegand, J.; McManis, J. S.; McCosar, B. H.; Weimar, W. R.; Brittenham, G. M.; Smith, R. E. J. Med. Chem. 1999, 42, 2432;
31. For a recent comprehensive review about chemistry of thiazoline, see (b) Gaumont, A.-C.; Gulea, M.; Levillain, J. Chem. Rev. 2009, 109, 1371.