New sources of chemical diversity inspired by biosynthesis: rational design of a potent epothilone analogue

Organic Letters

Volumn 11, Issue 15, 2009, Pages 3186-3189

  Frein, Jeffrey D ^a   Taylor, Richard E ^a   Sackett, Dan L ^b  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b EUNICE KENNEDY SHRIVER NATIONAL INSTITUTE OF CHILD HEALTH AND HUMAN DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(S) 14 METHOXYEPOTHILONE; (S)-14-METHOXYEPOTHILONE; DESOXYEPOTHILONE B; EPOTHILONE C; EPOTHILONE DERIVATIVE; MACROLIDE;

ARTICLE; CHEMISTRY; HUMAN; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE;

CELL LINE, TUMOR; EPOTHILONES; HUMANS; MACROLIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 68149091447     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900971r     Document Type: Article

References (26)

1. Ridley, C. P.; Lee, H. Y.; Khosla, C. Proc. Nat. Acad. Sci. U.S.A. 2008, 105, 4595-4600.
2. Kealey, J. T. Front. Biosci. 2003, 8, C1-C13.
3. Taylor, R. E.; Chen, Y.; Galvin, G. M.; Pabba, P. K. Org. Biomol. Chem. 2004, 2, 127-132.
4. Carlomagno, T.; Blommers, M. J. J.; Meiler, J.; Jahnke, W.; Schupp, T.; Peterson, F.; Schinzer, D.; Altmann, K.-H.; Griesinger, C Angew. Chem., Int. Ed. 2003, 42, 2511-2515.
5. An alternative binding conformation has been proposed on the basis of electron crystallography: Nettles, J. H.; Li, H.; Cornett, B.; Krahn, J. M.; Snyder, J. P.; Downing, K. H. Science 2004, 305, 866-869.
6. A critical review of published efforts toward identification of the binding conformation of the epothilones has been published: Heinz, D. W.; Schubert, W.-D.; Höfle, G. Angew. Chem., Int. Ed. 2005, 44, 1298-1301.
7. Taylor, R. E.; Chen, Y.; Beatty, A.; Myles, D. C.; Zhou, Y. J. Am. Chem. Soc. 2003, 125, 26-27.
8. Tang, L.; Shah, S.; Chung, L.; Carney, J.; Katz, L.; Khosla, C; Julien, B. Science 2000, 199, 640-642.
9. Chan, Y. A.; Boyne, M. T., II; Podevels, A. M.; Klimowicz, A. K.; Handelsman, J.; Kelleher, N. L.; Thomas, M. G. Proc. Nat. Acad. Sci. U.S.A. 2006, 103, 14349-14354.
10. Taylor, R. E.; Chen, Y. Org. Lett. 2001, 3, 2221-2224.
11. (a) Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048-6050.
12. (b) Jin, H.; Uenishi, J.-I.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 56445646.
13. Caserío, F. F.; Dennis, G. E.; DeWolfe, R. H.; Young, W. G. J. Am. Chem. Soc. 1955, 77, 4182-4183.
14. Taylor, R. E.; Haley, J. D. Tetrahedron Lett. 1997, 38, 2061-2064.
15. (a) Brown, H. C.; Jadhav, P. K.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535-1538.
16. (b) Hoffmann, R. W.; Kemper, B.; Metternich, R.; Lehmeier, T. Liebigs Ann. Chem. 1985, 2246-2260.
17. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512-519.
18. (a) Frigerio, M.; Santagostino, M.; Sputore, S. J. Org. Chem. 1999, 64, 4537-4538.
19. (b) Boeckman, R. K.; Shao, P.; Mullins, J. J. Org. Syn 2004, 77, 141-146.
20. Luche, J.-L.; Rodriguez-Hahn, L.; Crabbe, P. J. Chem. Soc., Chem. Commun. 1978, 601-602.
21. Slougui, N.; Rousseau, G. Synth. Commun. 1987, 17, 1-11.
22. Inukai, T.; Yoshizawa, R. J. Org. Chem. 1967, 32, 404-407.
23. Kiyooka, S.-I.; Kira, H.; Hena, M. A. Tetrahedron Lett. 1996, 37, 2597-2600.
24. Koch, G.; Loiseleur, O.; Fuentes, D.; Jantsch, A.; Altmann, K.-H. Org. Lett. 2002,4, 3811-3814.
25. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989-1993.
26. See: http://www.ixempra.com/.