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Synthesis of the C11-C21 Fragments of Epothilones A and B Using Ring-Closing Metathesis

  • Published : 2007.03.20

Abstract

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References

  1. Hofle, G.; Bedorf, N.; Gerth, K.; Reichenbach, H. German Patent DE 4138042, 1993
  2. Gerth, K.; Bedorf, N.; Hofle, G.;Irschik, H.; Reichenbach, H. J. Antibiot. 1996, 49, 560-563 https://doi.org/10.7164/antibiotics.49.560
  3. Hofle, G.; Bedorf, N.; Steinmetz, H.; Schomburg, D.; Gerth, K.; Reichenbach, H. Angew. Chem., Int. Ed. Engl. 1996, 35, 1567-1569 https://doi.org/10.1002/anie.199615671
  4. 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, 2325-2333
  5. Rivkin, A.; Chou, T.-C.; Danishefsky, S. J. Angew. Chem. Int. Ed. 2005, 44, 2838-2850 https://doi.org/10.1002/anie.200461751
  6. Harris, C. R.; Danishefsky, S. J. J. Org. Chem. 1999, 64, 8434-8456 https://doi.org/10.1021/jo991006d
  7. Nicolaou, K. C.; Roschangar, F.; Vourloumis, D. Angew. Chem. Int. Ed. 1998, 37, 2014-2045 https://doi.org/10.1002/(SICI)1521-3773(19980817)37:15<2014::AID-ANIE2014>3.0.CO;2-2
  8. White, J. D.; Carter, R. G.; Sundermann, K. F.; Wartmann, M. J. Am. Chem. Soc. 2001, 123, 5407-5413 https://doi.org/10.1021/ja010454b
  9. Mulzer, J.; Mantoulidis, A.; Oehler, E. Tetrahedron Lett. 1997, 38, 7725-7728 https://doi.org/10.1016/S0040-4039(97)10150-2
  10. Mulzer, J.; Mantoulidis, A.; Oehler, E. J. Org. Chem. 2000, 65, 7456-7467 https://doi.org/10.1021/jo0007480
  11. Lee, H. W.; Hong, Y. D.; Lee, I.-Y. C. Bull. Korean Chem. Soc. 1999, 20, 403-404
  12. Lee, H. W.; Lee, I. Y. C.; Hong, Y. D. Bull. Korean Chem. Soc. 2000, 21, 1177-1178
  13. Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450 https://doi.org/10.1016/S0040-4020(97)10427-6
  14. Chatterjee, A. K.; Choi, T.-L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370 https://doi.org/10.1021/ja0214882
  15. Kang, S. W.; Kim, S. H. Bull. Korean Chem. Soc. 2006, 27, 153-154 https://doi.org/10.5012/bkcs.2006.27.1.153
  16. Kim, A.; Hong, J. H. Bull. Korean Chem. Soc. 2006, 27, 976-980 https://doi.org/10.5012/bkcs.2006.27.7.976
  17. Yang, Z.; He, Y.; Vourloumis, D.; Vallberg, H.; Nicolaou, K. C. Angew. Chem. Int. Ed. Engl. 1997, 36, 166-168 https://doi.org/10.1002/anie.199701661
  18. Nicolaou, K. C.; Ninkovic, S.; Sarabia, F.; Vourloumis, D.; He, Y.; Vallberg, H.; Finlay, M. R. V.; Yang, Z. J. Am Chem. Soc. 1977, 119, 7974-7991 https://doi.org/10.1021/ja971110h
  19. Fürstner, A.; Mathes, C.; Grela, K. Chem. Commun. 2001, 1057-1059
  20. Fürstner, A.; Mathes, C.; Lehmann, C. W. Chem. Eur. J. 2001, 7, 5299-5317 https://doi.org/10.1002/1521-3765(20011217)7:24<5299::AID-CHEM5299>3.0.CO;2-X
  21. Taylor, R. E.; Chen, Y. Org. Lett. 2001, 3, 2221-2224 https://doi.org/10.1021/ol010094x
  22. 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, 757-759 https://doi.org/10.1002/anie.199707571
  23. Taylor, R. E.; Haley, J. D. Tetrahedron Lett. 1997, 38, 2061-2064 https://doi.org/10.1016/S0040-4039(97)00285-2
  24. 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, 2733-2734 https://doi.org/10.1021/ja964275j
  25. Kurosu, M.; Lorca, M. Tetrahedron Lett. 2002, 43, 1765-1769 https://doi.org/10.1016/S0040-4039(02)00139-9
  26. Corey, E. J.; Imwinkelried, R.; Pikul, S.; Xiang, Y. B. J. Am. Chem. Soc. 1989, 111, 5493-5495 https://doi.org/10.1021/ja00196a081
  27. Roush, W. R.; Hoong, L. K.; Palmer, M. A.; Straub, J. A.; Palkowitz, A. D. J. Org. Chem. 1990, 55, 4117-4126 https://doi.org/10.1021/jo00300a032
  28. Roush, W. R.; Hoong, L. K.; Palmer, M. A. J.; Park, J. C. J. Org. Chem. 1990, 55, 4109-4117 https://doi.org/10.1021/jo00300a031
  29. Yanagisawa, A.; Nakashima, H.; Ishiba, A.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 4723-4724 https://doi.org/10.1021/ja9603315

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