Synthesis, conformational analysis, and bioassay of 9,10-didehydroepothilone D

Organic Letters

Volumn 4, Issue 6, 2002, Pages 995-997

  White, James D ^a   Sundermann, Kurt F ^a   Wartmann, Markus ^a,b  

^a OREGON STATE UNIVERSITY   (United States)

^b NOVARTIS PHARMA AG   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

9,10 DEHYDROEPOTHILONE D; 9,10-DEHYDROEPOTHILONE D; ANTINEOPLASTIC AGENT; BIOPOLYMER; EPOTHILONE DERIVATIVE; THIAZOLE DERIVATIVE; TUBULIN;

ARTICLE; CELL DIVISION; CHEMISTRY; CONFORMATION; DRUG EFFECT; SYNTHESIS;

ANTINEOPLASTIC AGENTS; BIOPOLYMERS; CELL DIVISION; EPOTHILONES; MOLECULAR CONFORMATION; THIAZOLES; TUBULIN;

EID: 0037149679     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol020023d     Document Type: Article

References (16)

1. For recent reviews and perspectives, see: (a) Nicolaou, K. C.; Ritzen, A.; Namoto, K. Chem. Commun. 2001, 1523.
2. (b) Muizer, J. Monatsh. Chem. 2000, 131, 205.
3. (c) Altmann, K.-H.; Wartmann, M.; O'Reilly, T. Biochim. Biophys. Acta 2000, 1470, M79.
4. (d) Harris, C. R.; Danishefsky, S. J. J. Org. Chem. 1999, 64, 8434.
5. For a review of this aspect of epothilone pharmacology, see: Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem., Int. Ed. 1998, 37, 2014.
6. Attempts to obtain structural details of the interaction of epothilones with β-tubulin at atomic resolution have been unsuccessful thus far.
7. (a) White, J. D.; Carter, R. G.; Sundermann, K. F.J. Org. Chem. 1999, 64, 684.
8. (b) White, J. D.; Sundermann, K. F.; Carter, R. G. Org. Lett. 1999, 1, 1431.
9. White, J. D.; Carter, R. G.; Sundermann, K. F.; Wartmann, M. J. Am. Chem. Soc. 2001, 123, 5407.
10. For an early study of epothilone conformation, see; Victory, S. F.; Vander Velde, D. G.; Jalluri, R. K.; Grunewald, G. L.; Georg, G. I. Biorg. Med. Chem. Lett. 1996, 6, 893.
11. (a) Gerth, K.; Bedorf, N.; Höfle, G.; Irachik, H.; Reichenbach, H. J. Antibiot. 1996, 49, 960.
12. (b) Höfle, G.; Bedorf, N.; Steinmetz, H.; Schomburg, D.; Gerth, K.; Reichenbach, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1567.
13. Taylor, R. E.; Zajicek, J. J. Org. Chem. 1999, 64, 7224.
14. (a) Stephens, R. D.; Castro, C. E. J. Org. Chem. 1963, 28, 3313.
15. (b) Mignani, G.; Chevalier, C.; Grass, F.; Allmang, G.; Morel, D. Tetrahedron Lett. 1990, 31, 5161.
16. Inanaga, J.; Kirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.