Complex target-oriented total synthesis in the drug discovery process: The discovery of a highly promising family of second generation epothilones

Journal of the American Chemical Society

Volumn 125, Issue 10, 2003, Pages 2899-2901

  Rivkin, Alexey ^a   Yoshimura, Fumihiko ^a   Gabarda, Ana E ^a   Chou, Ting Chao ^a   Dong, Huajin ^a   Tong, William P ^a   Danishefsky, Samuel J ^a,b  

^a MEMORIAL SLOAN KETTERING CANCER CENTER   (United States)

^b Och Spine at New York Presbyterian Hospitals   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

12,13 DESOXYEPOTHILONE B; 9,10 DEHYDRO 12,13 DESOXYEPOTHILONE B; ANTINEOPLASTIC AGENT; EPOTHILONE DERIVATIVE; PACLITAXEL; UNCLASSIFIED DRUG; VINBLASTINE;

ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; NUDE MOUSE; PLASMA; TUMOR CELL LINE; TUMOR GROWTH;

ANTINEOPLASTIC AGENTS; CELL DIVISION; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; DRUG STABILITY; EPOTHILONES; HCT116 CELLS; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0037433593     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja029695p     Document Type: Article

References (26)

1. For extensive reviews in this field, see: (a) Harris, C. R.; Danishefsky, S. J. J. Org. Chem. 1999, 64, 8434.
2. (b) Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. 1998, 37, 2014.
3. (c) Additional references: Florsheimer, A.; Altmann, K. H. Expert Opin. Ther. Pat. 2001, 11, 951.
4. (d) Chou, T. C.; Zhang, X. G.; Harris, C. R.; Kuduk, S. D.; Balog, A.; Savin, K. A.; Bertino, J. R.; Danishefky, S. J. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 15798.
5. (e) Chou, T. C.; Zhang, X. G.; Balog, A.; Su, D.; Meng, D. F.; Savin, K.; Bertino, J. R.; Danishefsky, S. J. Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 9642.
6. Chou, T. C.; O'Connor, O. A.; Tong, W. P.; Guan, Y.; Zhang, Z.-G.; Stachel, S. J.; Lee, C.; Danishefsky, S. J. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 8113.
7. For more information about clinical trials of dEpoB, visit: www.kosan.com.
8. Rivkin, A.; Biswas, K.; Chou, T. C.; Danishefsky, S. J. Org. Lett. 2002, 4, 4081.
9. Rivkin, A.; Njardarson, J. T.; Biswas, K.; Chou, T. C.; Danishefsky, S. J. J. Org. Chem. 2002, 67, 7737.
10. White, J. D.; Carter, R. G.; Sundermann, K. F.; Wartmann, M. J. Am. Chem. Soc. 2001, 123, 5407.
11. (a) Balog, A.; Harris, C.; Savin, K.; Zhang, X. G.; Chou, T. C. Angew. Chem., Int. Ed. 1998, 37, 2675.
12. (b) Harris, C. R.; Kuduk, S. D.; Balog, A.; Savin, K.; Glunz, P. W.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 7050.
13. (c) Lee, C. B.; Wu, Z.; Zhang, F.; Chappell, M. D.; Stachel, S. J.; Chou, T. C.; Guan, Y.; Danishefsky, S. J. J. Am. Chem. Soc. 2001, 123, 5249.
14. (d) Biswas, K.; Lin, H.; Njardarson, J. T.; Chappell, M. D.; Chou, T. C.; Guan, Y.; Tong, W. P.; He, L.; Horwitz, S. B.; Danishefsky, S. J. J. Am. Chem. Soc. 2002, 124, 9825.
15. (a) Cohen, N.; Eichel, W. F.; Lopresti, R. J.; Neukom, C.; Saucy, G. J. Org. Chem. 1976, 41, 3505.
16. (b) Nagaoka, H.; Kishi, Y. Tetrahedron 1981, 37, 3873.
17. (c) Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348.
18. Chappell, M. D.; Stachel, S. J.; Lee, C. B.; Danishefsky, S. J. Org. Lett. 2000, 2, 1633.
19. Reviews: (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446.
20. (b) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18.
21. (c) Alkene Metathesis in Organic Chemistry; Fürstner, A., Ed.; Springer: Berlin, 1998.
22. (d) Fürstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012.
23. (e) Schrock, R. R. Top. Organomet. Chem. 1998, 1, 1.
24. For an early instance of macrocyclization in a complex setting via a RCM, see: Sinha, S. C.; Sun, J. Angew. Chem., Int. Ed. 2002, 41, 1381.
25. Hindupur, R. M.; Panicker, B.; Valluri, M.; Avery, M. A. Tetrahedron Lett. 2001, 42, 7341. Attempts to apply Avery's protocol for the installation of the thiazole gave the desired product in low yield and with poor E/Z selectivity.
26. Private communication from Professor