A highly stereoselective synthesis of epothilone B

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 684-685

  White, James D ^a   Carter, Rich G ^a   Sundermann, Kurt F ^a  

^a OREGON STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFUNGAL AGENT; EPOTHILONE B;

ARTICLE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0033525108     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo982108r     Document Type: Article

References (29)

1. Höfle, G.; Bedorf, N.; Gerth, H.; Reichenbach (GBF), DE-B 4138042, 1993; Chem. Abstr. 1993, 120, 52841.
2. Höfle, G.; Bedorf, N.; Steinmeth, H.; Schomburg, D.; Gerth, H.; Reichenbach, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1567.
3. For a recent review of the chemical biology of epothilones, see: Nicolaou, K. C.; Roschangar, F.; Vourloumis, F. Angew. Chem., Int. Ed. Engl. 1998, 37, 2014.
4. (a) Nicolaou, K. C.; Ninkovic, S.; Sarabia, F.; Vourloumis, D.; He, Y.; Vallberg, H.; Finlay, M. R. V.; Yang, Z. J. Am. Chem. Soc. 1997, 119, 7974.
5. (b) Meng, D.; Bertinato, P.; Balog, A.; Su, D.-S.; Kamenecka, T.; Sorensen, E. J.; Danishefsky, S. J. J. Am. Chem. Soc. 1997, 119, 10073.
6. (c) May, S. A.; Grieco, P. Chem. Commun. 1998, 1597.
7. (d) Schinzer, D.; Bauer, A.; Schieber, J. Synlett 1998, 861.
8. (a) Mulzer, J.; Mantoulidis, A. Tetrahedron Lett. 1996, 37, 9179.
9. (b) Claus, E.; Pahl, A.; Jones, P. G.; Meyer, H. M.; Kalesse, M. Tetrahedron Lett. 1997, 38, 1359.
10. (c) Gabriel, T.; Wessjohann, L. Tetrahedron Lett. 1997, 38, 1363.
11. (d) Taylor, R. E.; Haley, J. D. Tetrahedron Lett. 1997, 38, 2061.
12. (e) Brabander, J. D.; Rosset, S.; Bernardinelli, G. Synlett 1997, 824.
13. (f) Chakraborty, J. K.; Dutta, S. Tetrahedron Lett. 1998, 39, 101.
14. (g) Liu, Z.-Y.; Yu, C.-Z.; Yang, J. D. Synlett 1997, 1383.
15. (h) Liu, Z.-Y.; Yu, C.-Z.; Wang, R.-F.; Li, G. Tetrahedron Lett. 1998, 39, 5261.
16. (i) Mulzer, J.; Mantoulidis, A.; Ohler, E. Tetrahedron Lett. 1997, 38, 7725.
17. (j) Bijoy, P.; Avery, M. A. Tetrahedron Lett. 1998, 39 1209.
18. Duboudin, J. G.; Jousseaume, B.; Bonakdar, A. J. Organomet. Chem. 1979, 168, 227.
19. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1998, 110, 1238.
20. Evans, D. A.; Morrissey, M. M.; Dorow, R. L. J. Am. Chem. Soc. 1985, 107, 4346.
21. Davis, F. A.; Chaltophadhyay, S.; Towson, J. C.; Loi, S.; Reddy, T. J. Org. Chem. 1988, 53, 2087.
22. D = +3.5 (c 1.20).
23. Evans, D. A.; Ripin, D. H. B.; Johnson, J. S.; Shaughnessy, E. A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2117.
24. Schinzer, D.; Limberg, A.; Böhm, O. M. Chem. - Eur. J. 1996, 2, 1477.
25. Kim, S.; Park, J. H. Tetrahedron Lett. 1987, 28, 439.
26. For an analogous example of stereocontrolled aldol condensation via double chelation, see: White, J. D.; Porter, W. J.; Tiller, T. Synlett 1993, 535.
27. Inanaga, J.; Kirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
28. 3)).
29. Nicolaou, K. C.; Finlay, M. R. V.; Ninkovic, S.; Sarabia, F. Tetrahedron 1998, 54, 7127.