Total synthesis of epothilones B and D

Organic Letters

Volumn 3, Issue 14, 2001, Pages 2221-2223

  Taylor, Richard E ^a   Chen, Yue ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; BIOLOGICAL FACTOR; DESOXYEPOTHILONE B; EPOTHILONE B; EPOTHILONE DERIVATIVE; EPOXIDE; THIAZOLE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ALKENES; BIOLOGICAL FACTORS; CATALYSIS; EPOTHILONES; EPOXY COMPOUNDS; MOLECULAR STRUCTURE; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; THIAZOLES;

EID: 0035850272     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010094x     Document Type: Article

References (39)

1. (a) Höfle, G.; Bedorf, N.; Gerth, K.; Reichenbach, H. German Patent DE 4138042, 1993.
2. (b) Gerth, K.; Bedorf, N.; Höfle, G.; Irschik, H.; Reichenbach, H. J. Antibiot. 1996, 49, 560.
3. (c) Höfle, G.; Bedorf, N.; Steinmetz, H.; Schomburg, D.; Gerth, K., Reichenbach, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1567-1569.
4. (d) Bollag, D. M.; McQueney, P. A.; Zhu, J.; Hensens, O.; Koupal, L.; Liesch, J.; Goetz, M., Lazarides, E.; Woods, C. M. Cancer Res. 1995, 55, 2325.
5. (a) For a recent review of efforts to synthesize the epothilones, see: Mulzer, J. Monatsh. Chem. 2000, 131, 205.
6. (a) Su, D.-S.; Meng, D.; Bertinato, P.; Balog, A.; Sorensen, E. J.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L.; Horwitz, S. B. Angew. Chem., Int. Ed. Engl. 1997, 36, 757.
7. (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.
8. (c) Nicolaou, K. C.; Winssinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Giannakakou, P.; Hamel, E. Nature 1997, 387, 268.
9. (d) 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.
10. (e) Balog, A.; Harris, C. R.; Savin, K.; Zhang, X.-G.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem., Int. Ed. 1998, 37, 2675.
11. (f) Schinzer, D.; Bauer, A.; Schieber, J. Synlett 1998, 861.
12. (g) May, S. A.; Grieco, P. A. Chem. Commun. 1998, 1597.
13. (h) Mulzer, J.; Mantoulidis, A.; Öhler, E. Tetrahedron Lett. 1998, 39, 8633.
14. (i) White, J. D.; Carter, R. G.; Sundermann, K. F. J. Org. Chem. 1999, 64, 684.
15. (j) White, J. D.; Sundermann, K. F.; Carter, R. G. Org. Lett. 1999, 1, 1431.
16. (k) Nicolaou, K. C.; Hepworth, D.; Finlay, M. R. V.; King, N. P.; Werschkun, B.; Bigot, A. Chem. Commun. 1999, 519.
17. (l) Schinzer, D.; Bauer, A.; Schieber, J. Chem. Eur. J. 1999, 5, 2492.
18. (m) Harris, C. R.; Kuduk, S. D.; Balog, A.; Savin, K.; Danishefsky, S. J. Tetrahedron Lett. 1999, 40, 2263.
19. (n) Harris, C. R.; Kuduk, S. D.; Balog, A.; Savin, K.; Danishefsky, S. J. J. Am. Chem. Soc. 1999, 121, 7050.
20. (o) Martin, H. J.; Drescher, M.; Mulzer, J. Angew. Chem., Int. Ed. 2000, 39, 581.
21. (p) Sawada, D.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2000, 122, 10521.
22. (q) Mulzer, J.; Mantoulidis, A.; Öhler, E. J. Org. Chem. 2000, 65, 7456.
23. (a) Takai, K.; Tagashira, M.; Kuroda, T.; Oshima, K.; Utimoto, K.; Nozaki, H. J. Am. Chem. Soc. 1986, 108, 6048.
24. (b) Jin, H.; Uenishi, J.-I.; Christ, W. J.; Kishi, Y. J. Am. Chem. Soc. 1986, 108, 5644.
25. Caserio, F. F.; Dennis, G. E.; DeWolfe, R. H.; Young, W. G. J. Am. Chem. Soc. 1955, 77, 4182. From a mechanistic perspective, this reaction has been restudied on numerous occasions. However, to the best of our knowledge only Johnson has exploited the stereoselectivity of this interesting reaction from a synthetic perspective; Johnson, W. S.; Li, T.-T.; Harbert, C. A.; Bartlett, W. R.; Herrin, T. R.; Staskun, B.; Rich, D. H. J. Am. Chem. Soc. 1970, 92, 4461. See also: Taylor, R. E.; Ciavarri, J. P.; Hearn, B. R. Tetrahedron Lett. 1998, 39, 9361.
26. Caserio, F. F.; Dennis, G. E.; DeWolfe, R. H.; Young, W. G. J. Am. Chem. Soc. 1955, 77, 4182. From a mechanistic perspective, this reaction has been restudied on numerous occasions. However, to the best of our knowledge only Johnson has exploited the stereoselectivity of this interesting reaction from a synthetic perspective; Johnson, W. S.; Li, T.-T.; Harbert, C. A.; Bartlett, W. R.; Herrin, T. R.; Staskun, B.; Rich, D. H. J. Am. Chem. Soc. 1970, 92, 4461. See also: Taylor, R. E.; Ciavarri, J. P.; Hearn, B. R. Tetrahedron Lett. 1998, 39, 9361.
27. Caserio, F. F.; Dennis, G. E.; DeWolfe, R. H.; Young, W. G. J. Am. Chem. Soc. 1955, 77, 4182. From a mechanistic perspective, this reaction has been restudied on numerous occasions. However, to the best of our knowledge only Johnson has exploited the stereoselectivity of this interesting reaction from a synthetic perspective; Johnson, W. S.; Li, T.-T.; Harbert, C. A.; Bartlett, W. R.; Herrin, T. R.; Staskun, B.; Rich, D. H. J. Am. Chem. Soc. 1970, 92, 4461. See also: Taylor, R. E.; Ciavarri, J. P.; Hearn, B. R. Tetrahedron Lett. 1998, 39, 9361.
28. (a) Taylor, R. E.; Haley, J. Tetrahedron Lett. 1997, 38, 2061.
29. (b) Taylor, R. E.; Galvin, G. M.; Hilfiker, K. A.; Chen, Y. J. Org. Chem. 1998, 63, 9580.
30. (a) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827.
31. (b) Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401.
32. Aldehyde 2 was previously reported by Nicolaou (ref 3d).
33. Evans, D. A.; Ennis, M. D.; Mathre, D. J. J. Am. Chem. Soc. 1982, 104, 1737.
34. Kamiya, N.; Chikami, Y.; Ishii, Y. Synlett 1990, 675.
35. Kiyooka, S.-I.; Kira, H.; Hena, M. A. Tetrahedron Lett. 1996, 37, 2597.
36. Kikkawa, I.; Yorifuji, T. Synthesis 1980, 877.
37. Inanaga, J.; Hirata, K.; Saeki, H.; Katsuki, T.; Yamaguchi, M. Bull. Chem. Soc. Jpn. 1979, 52, 1989.
38. Satisfactory spectroscopic and HRMS data have been obtained for all compounds.
39. Taylor, R. E.; Zajicek, J. J. Org. Chem. 1999, 64, 7224.