The synthesis of epothilones: Highlights from a year's race

Chemtracts

Volumn 11, Issue 9, 1998, Pages 678-696

  Appendino, Giovanni ^a   Casiraghi, Giovanni ^b  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

EPOTHILONE A; EPOTHILONE B; MACROLIDE; PACLITAXEL; PACLITAXEL DERIVATIVE;

CYCLIZATION; CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; EPOXIDATION; REACTION ANALYSIS; SHORT SURVEY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0031791794     PISSN: 14319268     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Short Survey

References (49)

1. (a) Höfle, G., Bedorf, K., Gerth, K., Reichenbach, H. DE-4138042 1993. Chem. Abstr. 1993, 119, 180598
2. (b) Gerth, K., Bedorf, N., Höfle, G., Irsshick, H., Reichenbach, H. J. Antibiot. 1996, 49, 560.
3. Bollag, D.M., McQueney, P.A., Zhu, J., Hensen, O., Koupal, L., Liesch, J., Goetz, M., Lazarides, E., Wood, C.M. Cancer Res. 1995, 55, 2325.
4. Höfle, G., Bedorf, N., Steinmetz, H., Schomburg, D., Gerth, D., Reichenbach, H. Angew. Chem. Int. Ed. Engl. 1996, 35, 1567.
5. Balog, A., Meng, D., Kamenecka, T., Bertinato, P., Su, D.-S., Sorensen, E.J., Danishefsky, S.J. Angew. Chem. Int. Ed. Engl. 1996, 35, 2801.
6. (a) Service, R.F. Science 1996, 274, 2009
7. (b) Mann, J. Nature 1997, 385, 117
8. (c) Cameron, J.C., Paterson, J. Nature 1997, 387, 238. Epothilones were also featured in an Angewandte Chemie article by L. Wessjohann (1997, 36, 715), and in an article in Spectrum der Wissenshaft by D. Schinzer and A. Limberg (1997, 38).
9. (c) Cameron, J.C., Paterson, J. Nature 1997, 387, 238. Epothilones were also featured in an Angewandte Chemie article by L. Wessjohann (1997, 36, 715), and in an article in Spectrum der Wissenshaft by D. Schinzer and A. Limberg (1997, 38).
10. (c) Cameron, J.C., Paterson, J. Nature 1997, 387, 238. Epothilones were also featured in an Angewandte Chemie article by L. Wessjohann (1997, 36, 715), and in an article in Spectrum der Wissenshaft by D. Schinzer and A. Limberg (1997, 38).
11. McDaniel, R., Ebert-Khosla, S., Hopwood, D.A., Khosla, C. Nature 1995, 375, 549.
12. Meng, D., Bertinato, P., Balog, A., Su, D.-S., Kamenecka, T., Sorensen, E.J., Danishefsky, S.J. J. Am. Chem. Soc. 1997, 119, 10073.
13. Schinzer, D., Limberg, A., Bauer, A., Böhm, O.M., Cordes, M. Angew. Chem. Int. Ed. Engl. 1997, 36, 523.
14. Nicolaou, K.C., Sarabia, S., Ninkovic, S., Yang, Z. Angew. Chem. Int. Ed. Engl. 1997, 36, 525.
15. Nicolaou, K.C., He, Y., Vourloumis, D., Vallberg, H., Roschangar, F., Sarabia, F., Ninkovic, S., Yang, Z., Trujillo, J.I. J. Am. Chem. Soc. 1997, 119, 7960.
16. Nicolaou, K.C., Vallberg, H., King, N.P., Roschanger, F., He, Y., Vourloumis, D., Nicolaou, C.G. Chem. Eur. J. 1997, 3, 1957.
17. Nicolaou, K.C., Sarabia, F., Finlay, M.R.V., Ninkovic, S., King, N.P., Vourloumis, D., He, Y. Chem. Eur. J. 1997, 3, 1971.
18. 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.
19. Meng, D., Sorensen, E.J., Bertinato, P., Danishefsky, S.J. J. Org. Chem. 1996, 67, 7998.
20. Bertinato, P., Sorensen, E.J., Meng, D., Danishefsky, S.J. J. Org. Chem. 1996, 67, 8000.
21. 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.
22. Hayward, C.M., Yohannes, D., Danishefsky, S.J. J. Am. Chem. Soc. 1993, 115, 9345. A risky ester enolate bond construction is also portrayed in Danishefsky's synthesis of quadrone, see: Danishefsky, S.J., Vaughan, K., Gadawood, R., Tsuzuki, K. J. Am. Chem. Soc. 1981, 103, 4136.
23. Hayward, C.M., Yohannes, D., Danishefsky, S.J. J. Am. Chem. Soc. 1993, 115, 9345. A risky ester enolate bond construction is also portrayed in Danishefsky's synthesis of quadrone, see: Danishefsky, S.J., Vaughan, K., Gadawood, R., Tsuzuki, K. J. Am. Chem. Soc. 1981, 103, 4136.
24. For a review on this and other palladium-catalyzed cross-coupling reactions of organoboron compounds, see: Miyaura, N., Suzuki, A. Chem. Rev. 1995, 95, 2457.
25. Schinzer, D., Limberg, A., Böhm, O.M. Chem. Eur. J. 1996, 2, 1477.
26. Nicolaou, K.C., He, Y., Vourloumis, D., Vallberg, H., Ynag, Z. Angew. Chem. Int. Ed. Engl. 1996, 35, 2399.
27. 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.
28. Nicolaou, K.C., Vourloumis, D., Li, T., Pastor, J., Winssinger, N., He, Y, Ninkovic, S., Sarabia, F., Vallberg, H., Roschangar, F., King, N.P., Finlay, M.R.V., Giannakakou, P., Verdier-Pinard, P., Hamel, E. Angew. Chem. Int. Ed. Engl. 1997, 36, 2097.
29. Meng, D., Su, D.-S., Balog, A., Bertinato, P., Sorensen, E.J., Danishefsky, S.J., Zheng, Y-H., Chou, T.-C., He, L., Horwitz, S.B. J. Am. Chem. Soc. 1997, 119, 2733.
30. For a recent review, see: Schuster, M., Blechert, S. Angew. Chem. Int. Ed. Engl. 1997, 36, 2037.
31. Schwab, P., France, M.B., Ziller, J.W., Grubbs, R.H. Angew. Chem. Int. Ed. Engl. 1995, 34, 2039.
32. Schrock, R.R., Murzdek, J.S., Bazan, G.C., Robbins, J., DiMare, M., O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875.
33. Nicolaou, K.C., Xiao, X.-Y., Parandoosh, Z., Senyei, A., Nova, M.P. Angew. Chem. Int. Ed. Engl. 1995, 34, 2289.
34. Available from IRORI Quantum Microchemistry, San Diego, CA.
35. Inanga, J., Hirata, K., Saeki, H., Katsuki, T., Yamaguchi, M. Bull. Chem. Soc., Japan 1979, 52, 1989. For a recent review on macrolide synthesis, see: Back, T.G. Tetrahedron 1997, 33, 3041.
36. Inanga, J., Hirata, K., Saeki, H., Katsuki, T., Yamaguchi, M. Bull. Chem. Soc., Japan 1979, 52, 1989. For a recent review on macrolide synthesis, see: Back, T.G. Tetrahedron 1997, 33, 3041.
37. Rathke, M.W., Sullivan, D.F. J. Am. Chem. Soc. 1973, 95, 3050.
38. Enders, D., Eichenhauer, H. Chem. Ber. 1979, 112, 2933.
39. Inukai, T., Yoshizawa, R. J. Org. Chem. 1967, 32, 404.
40. Nicolaou, K.C., Ninkovic, S., Finlay, M.R.V., Sarabia, F., Li, T. Chem. Commun. 1997, 2343.
41. For a recent review on the use of the Wittig reaction in the construction of complex natural products, see: Nicolaou, K.C., Härtel, M.W., Gunzner, J.L., Nadin, A. Liebigs Ann./Recueil 1997, 1283.
42. Racherla, U.S., Brown, H.C. J. Org. Chem. 1991, 56, 401.
43. Su, D.-S., Balog, A., Meng, D., Bertinato, P., Danishefsky, S.J., Zheng, Y.-H., Chou, T.-C., He, L., Horwitz, S.B. Angew. Chem. Int. Ed. Engl. 1997, 36, 2093.
44. For a comprehensive study of the structure-activity relationships in taxoids, see: (a) Chen, S.-H., Farina, V. In The Chemistry and Pharmacology of Taxol and its Derivatives, Farina, V., ed., Elsevier: New York, 1995, pp. 165-253; and Georg, G.I., Böge, T.C., Cheruvallath, Z.S., Clowers, J.S., Harriman, G.B.C., Hepperle, M., Park, H. In Taxol: Science and Applications, Suffness, M., ed. CRC: Boca Raton, FL, 1995, pp. 317-375.
45. For a comprehensive study of the structure-activity relationships in taxoids, see: (a) Chen, S.-H., Farina, V. In The Chemistry and Pharmacology of Taxol and its Derivatives, Farina, V., ed., Elsevier: New York, 1995, pp. 165-253; and Georg, G.I., Böge, T.C., Cheruvallath, Z.S., Clowers, J.S., Harriman, G.B.C., Hepperle, M., Park, H. In Taxol: Science and Applications, Suffness, M., ed. CRC: Boca Raton, FL, 1995, pp. 317-375.
46. Nicolaou, K.C., van Deft, F., Ohshima, T., Vourloumis, D., Xu, J., Hosokawa, S., Pfefferkorn, J., Kim, S., Li, T. Angew. Chem. Int. Ed. Engl. 1997, 36, 2520.
47. Nogales, E., Wolf, S., Downing, K.H. Nature 1998, 391, 199.
48. Time, January 2, 1961. (Quoted in Time, Winter Special Issue 1997-1998, p. 121.)
49. Time, January 2, 1961. (Quoted in Time, Winter Special Issue 1997-1998, p. 121.)