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N-Methyl Pseudoephedrine-mediated Asymmetric Syntheses of Dihydroquinoxalinones for the Preparation of Flavane Analogues

  • Kim, Yong-Tae (Department of Chemistry and Bio/Molecular Informatics Center, Konkuk University) ;
  • Kang, Kyoung-Hee (Department of Chemistry and Bio/Molecular Informatics Center, Konkuk University) ;
  • Choi, Eui-Ta (Department of Chemistry and Bio/Molecular Informatics Center, Konkuk University) ;
  • Lee, Min-Hee (Department of Chemistry and Bio/Molecular Informatics Center, Konkuk University) ;
  • Park, Yong-Sun (Department of Chemistry and Bio/Molecular Informatics Center, Konkuk University)
  • Published : 2007.02.20

Abstract

Keywords

References

  1. Nam, J.; Lee, S.-k.; Park, Y. S. Tetrahedron 2003, 59, 2397 https://doi.org/10.1016/S0040-4020(03)00285-0
  2. Lee, S.-k.; Nam, J.; Park, Y. S. Synlett 2002, 790
  3. Nam, J.; Lee, S.-k.; Kim, K. Y.; Park, Y. S. Tetrahedron Lett. 2002, 42, 8253
  4. Mahaney, P. E.; Webb, M. B.; Ye, F.; Sabatucci, J. P.; Steffan, R. J.; Chadwick, C. C.; Harnish, D. C.; Trybulski, E. J. Bioorg. Med. Chem. 2006, 14, 3455 https://doi.org/10.1016/j.bmc.2006.01.001
  5. Ha, S. N.; Hey, P. J.; Ransom, R. W.; Harrell, M.; Murphy, K. L.; Chang, R.; Chen, T.-B.; Su, D.-S.; Markowitz, M. K.; Bock, M. G.; Freidinger, R. M.; Hess, F. J. Biochem. Biophys. Res. Commun. 2005, 331, 159 https://doi.org/10.1016/j.bbrc.2005.03.142
  6. Gupta, D.; Ghosh, N. N.; Chandra, R. Bioorg. Med. Chem. Lett. 2005, 15, 1019 https://doi.org/10.1016/j.bmcl.2004.12.041
  7. Su, D.-S.; Markowitz, M. K.; Dipardo, R. M.; Murphy, K. L.; Harrell, C. M.; O'Malley, S. S.; Ransom, R. W.; Chang, R. S. L.; Ha, S.; Hess, F. J.; Pettibone, D. J.; Mason, G. S.; Boyce, S.; Freidinger, R. M.; Bock, M. G. J. Am. Chem. Soc. 2003, 125, 7516 https://doi.org/10.1021/ja0353457
  8. Tung, C.-L.; Sun, C.-M. Tetrahedron Lett. 2004, 45, 1159
  9. Jamieson, C.; Congreve, M. S.; Emiabata-Smith, D. F.; Ley, S. V.; Scicinski, J. J. Org. Process. Res. Dev. 2002, 6, 823
  10. Holland, R. J.; Hardcastle, I. R.; Jarman, M. Tetrahedron Lett. 2002, 43, 6435 https://doi.org/10.1016/S0040-4039(02)01363-1
  11. Laborde, E.; Peterson, B. T.; Robinson, L. J. Comb. Chem. 2001, 3, 572 https://doi.org/10.1021/cc010025+
  12. Kim, Y.; Shin, E.-k.; Beak, P.; Park, Y. S. Synthesis 2006, 3805
  13. Park, Y. S.; Yum, E. K.; Basu, A.; Beak, P. Org. Lett. 2006, 8, 2667 https://doi.org/10.1021/ol0604015
  14. Coldham, I.; Dufour, S.; Haxell, T. F. N.; Howard, S.; Vennall, G. P. Angew. Chem. Int. Ed. 2002, 41, 3887 https://doi.org/10.1002/1521-3773(20021018)41:20<3887::AID-ANIE3887>3.0.CO;2-J
  15. Clayden, J.; Mitjans, D.; Youssef, L. H. J. Am. Chem. Soc. 2002, 124, 5266 https://doi.org/10.1021/ja017702o
  16. Nakamura, S.; Nakagawa, R.; Watanabe, Y.; Toru, T. J. Am. Chem. Soc. 2000, 122, 11340 https://doi.org/10.1021/ja0025191
  17. Kim, H. J.; Kim, Y.; Choi, E. T.; Lee, M. H.; No, E. S.; Park, Y. S. Tetrahedron 2006, 62, 6303 https://doi.org/10.1016/j.tet.2006.04.045
  18. Shin, E.-k.; Chang, J.-y.; Kim, H. J.; Kim, Y.; Park, Y. S. Bull. Korean Chem. Soc. 2006, 27, 447 https://doi.org/10.5012/bkcs.2006.27.3.447
  19. Chang, J.-y.; Shin, E.-k.; Kim, H. J.; Kim, Y.; Park, Y. S. Bull. Korean Chem. Soc. 2005, 26, 989 https://doi.org/10.5012/bkcs.2005.26.6.989
  20. Treweeke, N. R.; Hitchcock, P. B.; Pardoe, D. A. Caddick, S. Chem. Commun. 2005, 1868
  21. Chang, J.-y.; Shin, E.-k.; Kim, H. J.; Kim, Y.; Park, Y. S. Tetrahedron 2005, 61, 2743 https://doi.org/10.1016/j.tet.2005.01.091
  22. Valenrod, Y.; Myung, J.; Ben, R. N. Tetrahedron Lett. 2004, 45, 2545 https://doi.org/10.1016/j.tetlet.2004.02.004
  23. Devine, P. N.; Foster, B. S.; Grabowski, E. J. J.; Reider, P. J. Heterocycles 2002, 58, 119 https://doi.org/10.3987/COM-02-S(M)54
  24. Caddick, S.; Afonso, C. A. M.; Candeias, S. X.; Hitchcock, P. B.; Jenkins, K.; Murtagh, L.; Pardoe, D.; Santos, A. G.; Treweeke, N. R.; Weaving, R. Tetrahedron 2001, 57, 6589 https://doi.org/10.1016/S0040-4020(01)00550-6
  25. Ben, R. N.; Durst, T. J. Org. Chem. 1999, 64, 7700 https://doi.org/10.1021/jo9811625
  26. Kim, Y.; Lee, M. H.; Choi, E. T.; No, E. S.; Park, Y. S. Heterocycles 2007, 71, 5 https://doi.org/10.3987/COM-06-10910
  27. Li, Y.-Z.; Townshend, A. Anal. Chim. Acta 1997, 340, 159
  28. Li, X.; Wang, D.; Wu, J.; Xu, W. Heterocycles 2005, 65, 2741 https://doi.org/10.3987/COM-05-10461
  29. Kim, K. S.; Qian, L.; Bird, J. E.; Dickinson, K. E. J.; Moreland, S.; Schaeffer, T. R.; Waldron, T. L.; Delaney, C. L.; Weller, H. N.; Miller, A. V. J. Med. Chem. 1993, 36, 2335 https://doi.org/10.1021/jm00068a010

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