Epoxide opening with acetylide for synthesis of epothilone A C7-21 segment

Tetrahedron Letters

Volumn 39, Issue 29, 1998, Pages 5261-5264

  Liu, Zhi Yu ^a   Yu, Chen Zhi ^a   Wang, Rui Fang ^a   Li, Gang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EPOTHILONE A; EPOXIDE;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032537693     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01060-0     Document Type: Article

References (22)

1. 1. (a) Höfle, G.; Bedorf, N.; Gerth, K. and Reichenach, H., DE 4, 138, 042, 1993, Chem. Abstr., 1993, 120, 52841;
2. (b) Höfle, G.; Bedorf, N.; Steinmertz, H.; Schomburg, D.; Gerth, K. and Reichenbach, H., Angew. Chem. Int. Ed. Engl. 1996, 35, 1567.
3. 2. Bollag, D. M.; Mcqueney, P. A.; Zhu, J.; Kaupal, L.; Leisch, J.; Goetz, M.; Lazarides, E. and Woods, C. M., Cancer Res., 1995, 55, 2325.
4. 3. A)Balog, A.; Meng, D.; Kamenecka, T.; Bertinato, P.; Su, D.-S.; Sorensen, E. J. and Danishefsky, S. J., Angew. Chem. Int. Ed. Engl. 1996, 35, 2801;
5. b)Meng, D.; Su, D.-S.; Balog, A.; Bertinato, P.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L. and Horwitz, S. B., J. Am. Chem. Soc., 1997. 119, 2733;
6. c)Su, D.-S.; Meng, D.; Bertinato, P.; Balog, A.; Sorensen, E. J.; Danishefsky, S. J.; Zheng, Y.-H.; Chou, T.-C.; He, L. and Horwitz, S. B., Angew. Chem. Int. Ed. Engl., 1997, 36, 757 and cited references therein.
7. 4. (a) Nicolaou, K. C.; Sarabia, F. and Yang, Z., Angew. Chem. Int. Ed. Engl., 1997, 36, 525 and cited reference therein;
8. (b) Nicoloau, K. C.; Winssinger, N.; Pastor, J.; Ninkovic, S.; Sarabia, F.; He, Y.; Vourloumis, D.; Yang, Z.; Li, T.; Glannakakou P. and Hamel, E., Nature, 1997, 387, 15.
9. 5. Schinzer, D.; Limberg, A.; Bauer, A.; Böhm, O. M. and Cordes, M., Angew. Chem. Int. Ed. Engl., 1997, 36, 523 and cited reference therein.
10. 6. Mulzer, J. and Mantoulidis, A., Tetrahedron Lett., 1996, 37, 9179.
11. 7. Claus, E.; Pahl, A.; Jones, P. G.; Meyer, H. M. and Kalesse, M., Tetrahedron Lett., 1997, 38, 1359.
12. 8. Gabriel, T. and Wessjohann, L., Tetrahedron Lett., 1997, 38, 1363.
13. 9. Brabander, J.D.; Rosset, S.; Bernardinelli, G., Synlett, 1997, 824.
14. 10. Liu, Z.-Y.; Yu, C.-Z.; Yang, J.-D., Synlett, 1997, 1383.
15. 11. All the yields mentioned in this paper are not optimum.
16. 12. (a) the compound 9 was prepared from vitamin C with the modification of the Abushanab's procedure: Abushanab, E.; Vemishetti, P.; Leiby, R. W.; Singh, H.K.; Mikkilineni, A.B.; Wu, D.C.-J.; Saibaba, R.; Panzica, R.P., J.Org. Chem., 1988, 53, 2598.
17. (b)Abushanab, e.;Bessodes, M.; Antonakis., Tetrahedron Lett., 1984, 25, 3841.
18. 13. Zhao, Z.; Scarlato, G.R.; Armstrong, R.W., Tetrahedron Lett., 1991, 32, 1609.
19. 14. Hooper, F.E.; Johnson, T.B.; J.Am.Chem.Soc., 1934, 56, 470.
20. 15. Zhong Y.-L. and Shing, T. K. M., J. Org. Chem., 1997, 62, 2622-2624.
21. 3): 9.59(s, 1H), 6.95(s, 1H), 6.48(d, J=4.45Hz, 1H), 5.46-5.41(m, 2H), 4.66(d, J=6.63Hz, 1H), 4.51(d, J=6.62Hz, 1H), 4.09(t, J=6.86Hz, 1H), 3.37(s, 3H), 2.70(s, 3H), 2.44-2.28(m, 3H), 2.08-1.98(m, 5H), 1.72-1.67(m, 2H), 1.44-1.31(m, 2H), 1.07(d, J=7.01Hz, 3H). MS(m/e): 352(M+1, 1.31), 306(0.66), 290(18.94), 272(0.96), 212(89.68), 166(17.42), 152(19.22).
22. 7-15 segment: Bijoy, P.; Avery, M. A., Tetrahedron Lett., 1998, 39, 209.