Total synthesis of chloptosin, a potent apoptosis-lnducing cyclopeptide

Organic Letters

Volumn 12, Issue 5, 2010, Pages 1124-1127

  Yu, Shun Ming ^a   Hong, Wen Xu ^a   Wu, Yuan ^a   Zhong, Chun Long ^a   Yao, Zhu Jun ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CHLOPTOSIN; CYCLOPEPTIDE; PYRIDAZINE DERIVATIVE;

ANIMAL; APOPTOSIS; ARTICLE; CATALYSIS; CHEMISTRY; DRUG EFFECT; HUMAN; MOUSE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SYNTHESIS; TUMOR CELL LINE;

ANIMALS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CATALYSIS; CELL LINE, TUMOR; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MICE; PEPTIDES, CYCLIC; PYRIDAZINES;

EID: 77749298166     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100135a     Document Type: Article

References (30)

1. (a) Steller, H. Science 1995, 267, 1445-1449.
2. (b) Ashkenazi, A.; Dixit, V. M. Science 1998, 281, 1305-1308.
3. (a) Ling, Y.-H.; Priebe, W.; Perez-Soler, R. Cancer Res. 1993, 53, 1845-1852.
4. (b) Haldar, S.; Chintapalli, J.; Croce, C. M. Cancer Res. 1996, 56, 1253-1255.
5. Umezawa, K.; Ikeda, Y.; Uchihata, Y.; Naganawa, H.; Kondo, S. J. Org. Chem. 2000, 65, 459-463.
6. (a) Kamenecka, T. M.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1998, 37, 2993-2995.
7. (b) Kamenecka, T. M.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1998, 37, 2995-2998.
8. (c) Kamenecka, T. M.; Danishefsky, S. J. Chem.-Eur. J. 2001, 7, 41-63.
9. (a) Depew, K. M.; Marsden, S. P.; Zatorska, D.; Zatorski, A.; Bornmann, W. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 1195311963.
10. (b) Nishida, A.; Ushigome, S.; Sugimoto, A.; Arai, S. Heterocycles 2005, 66, 181-185.
11. (c) Iwaki, T.; Yamada, F.; Funaki, S.; Somei, M. Heterocyles 2005, 65, 1811-1815.
12. (d) Kawahara, M.; Nishida, A.; Nakagawa, M. Org. Lett. 2000, 2, 675-678.
13. (e) Sun, W. Y.; Sun, Y.; Tang, Y. C.; Hu, J. Q. Syelett 1993, 337-338.
14. (a) Hong, W.-X.; Yao, Z.-J. Chin. J. Chem. 2004, 22, 365-370.
15. (b) Kim, Y.-A.; Han, S.-Y. Svnth. Commun. 2004, 34, 2931-2943.
16. Hong, W. X.; Chen, L. J.; Zhong, C. L.; Yao, Z.-J. Org. Lett. 2006, 8, 4919-4922.
17. A review on the bidirectional synthesis, see: Poss, C. S.; Schreiber, S. L. Acc. Chem. Res. 1994, 27, 9-17.
18. Xia, Y. X.; Zhu, J. P. Synlett 2005, 16, 2469-2472.
19. (a) August, R. A.; Khan, J. A.; Moody, C. M.; Young, D. W. J. Chem. Soc., Perkin Trans. I. 1996, 507-514.
20. (b) Johannesson, P. J. Med. Chem. 1999, 42, 4524-4537.
21. Ley, S. V.; Cleator, E.; Hewitt, P. R. Org. Biomol. Chem. 2003, 1, 3492-3494.
22. (a) Li, P.; Xu, J. C. Tetrahedron 2000, 56, 8119-8131.
23. (b) Li, P.; Xu, J. C. Chem. Lett. 2000, 204-205.
24. (a) Hale, K. J.; Lazarides, L. Org. Lett. 2002, 4, 1903-1906.
25. (b) Hale, K. J.; Delisser, V. M.; Yeh, L.-K.; Peak, S. A.; Manaviazar, S.; Bhatia, G. S. Tetrahedron Lett. 1994, 35, 7685-7688.
26. (c) Hale, K. J.; Cai, J.; Delisser, V.; Manaviazar, S.; Peak, S. A.; Bhatia, G. S.; Collins, T. C.; Jogiya, N. Tetrahedron 1996, 52, 1047-1068.
27. Carpino, L. A.; Cohen, B. J.; Stephens, K. E., Jr.; Sadat-Aalaee, S. Y.; Tien, J. H.; Langridge, D. C. J. Org. Chem. 1986, 51, 3732-3734.
28. Hale, K. J.; Cai, J.; Williams, G. Synlett. 1998, 149-152.
29. Grotenbreg, G. M.; Timmer, M. S.; Llamas-Saiz, A. L.; Verdoes, M.; van der Marel, G. A.; van Raaij, M. J.; Overkleeft, H. S.; Overhand, M. J. Am. Chem. Soc. 2004, 126, 3444-3446.
30. Cao, B.; Park, H.; Joullie, M. M. J. Am. Chem. Soc. 2002, 124, 520-521.