Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Concise Synthesis of Stemofurans A, C, and Derivatives

  • Lee, Hee-Jin (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Kim, Sung-Hong (Analysis Research Division, Daegu Center, Korea Basic Science Institute) ;
  • Lee, Yong-Rok (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Wang, Xue (School of Chemical Engineering & Food Science, Xiangfan University) ;
  • Lyoo, Won-Seok (School of Textiles, Yeungnam University)
  • Received : 2010.08.21
  • Accepted : 2010.08.30
  • Published : 2010.10.20
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References

  1. Pacher, T.; Segar, C.; Engelmeier, D.; Vajrodaya, S.; Hofer, O.; Greger, H. J. Nat. Prod. 2002, 65, 820. https://doi.org/10.1021/np0105073
  2. Adams, M.; Pacher, T.; Greger, H.; Bauer, R. J. Nat. Prod. 2005, 68, 83. https://doi.org/10.1021/np0497043
  3. Bauer, R. In Bioassay Methods in Natural Product and Drug Development; Bohlin, L., Bruhn, J. C., Eds.; Kluwer Academic Publishers: Dorrecht, 1999; p 119.
  4. Adams, M.; Kunert, O.; Bauer, R. Planta Med. 2004, 70, 904. https://doi.org/10.1055/s-2004-832614
  5. Pharmacopoeia of the Peoples Republic of China; Chemical Industry Press: Beijing, 2000; Vol. 1, p 199.
  6. Do, T. L. Vietnamese Traditional Medicinal Plants and Drugs, 3rd ed.; Publishing House of Medicine: Hanoi, 2001; p 162.
  7. Zhao, W. M.; Qin, G. W.; Ye, Y.; Xu, R. S.; Le, X. F. Phytochemistry1995, 38, 711. https://doi.org/10.1016/0031-9422(94)00655-D
  8. Pasturel, J. Y.; Solladie, G.; Maignan, J. Fr. Demande FR 2833259, 2003; Chem. Abstr. 2003, 139, 36375.
  9. Miyata, O.; Takeda, N.; Naito, T. Org. Lett. 2004, 6, 1761. https://doi.org/10.1021/ol049564o
  10. Takeda, N.; Miyata, O.; Naito, T. Eur. J. Org. Chem. 2007, 1491.
  11. Lee, H. J.; Lee, Y. R.; Kim, S. H. Helv. Chim. Acta 2009, 92, 1404. https://doi.org/10.1002/hlca.200900014
  12. Miyaura, N.; Suzuki, A. Chem. Rev. 1995, 95, 2457. https://doi.org/10.1021/cr00039a007
  13. Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J.,Eds.; Wiley-VCH: New York, 1998.
  14. Handbook of Organopalladium Chemistry for Organic Synthesis; Negishi, E.-I., Ed.; Wiley-Interscience: New York, 2002.
  15. Takasugi, M.; Nagao, S.; Ueno, S.; Masamune, T.; Shirata, A.; Takahashi, K. Chem. Lett. 1978, 1239.
  16. Fukai, T.; Nomura, T. Phytochemistry 1995, 38, 759. https://doi.org/10.1016/0031-9422(94)00674-I
  17. Fukai, T.; Sheng, C.-B.; Horikoshi, T.; Nomura, T. Pyotochemistry 1996, 43, 1119. https://doi.org/10.1016/S0031-9422(96)00391-3
  18. Na, M.; Hoang, D. M.; Njamen, D.; Mbafor, J. T.; Fomum, Z. T.;Thuong, P. T.; Ahn, J. S.; Oh, W. K. Bioorg. Med. Chem. Lett.2007, 17, 3868. https://doi.org/10.1016/j.bmcl.2007.05.005
  19. Lee, Y. R.; Choi, J. H.; Yoon, S. H. Tetrahedron Lett. 2005, 46, 7539. https://doi.org/10.1016/j.tetlet.2005.08.159
  20. Lee, Y. R.; Lee, W. K.; Noh, S. K.; Lyoo, W. S. Synthesis 2006, 853.
  21. Lee, Y. R.; Kim D. H. Synthesis 2006, 603.
  22. Lee, Y. R.; Kim, J. H. Synlett 2007, 2232.
  23. Wang, X.; Lee, Y. R. Tetrahedron Lett. 2007, 48, 6275. https://doi.org/10.1016/j.tetlet.2007.07.022
  24. Wang, X.; Lee, Y. R. Synthesis 2007, 3044.
  25. Lee, Y. R.; Xia, L. Synthesis 2007, 3240.
  26. Lee, Y. R.; Kim, Y. M. Helv. Chim. Acta 2007, 90, 2401. https://doi.org/10.1002/hlca.200790247
  27. Lee, Y. R.; Li, X.; Kim, J. H.; J. Org. Chem. 2008, 73, 4313. https://doi.org/10.1021/jo800367r
  28. Xia, L.; Lee, Y. R. Synlett 2008, 1643.
  29. Lee, Y. R.; Hung, T. V. Tetrahedron 2008, 64, 7338. https://doi.org/10.1016/j.tet.2008.05.053
  30. Lee, Y. R.; Xia, L. Tetrahedron Lett. 2008, 49, 3283. https://doi.org/10.1016/j.tetlet.2008.03.075
  31. Lee, Y. R.; Wang, X. Tetrahedron 2009, 65, 10125. https://doi.org/10.1016/j.tet.2009.10.045
  32. Lee, Y. R.; Kim, Y. M.; Kim. S. H. Tetrahedron 2009, 65, 101. https://doi.org/10.1016/j.tet.2008.10.101
  33. Jung, D, H.; Lee, Y. R.; Kim, S. H. Helv. Chim. Acta 2010, 93, 635. https://doi.org/10.1002/hlca.200900251
  34. Saimoto, H.; Yoshida, K.; Murakami, T.; Morimoto, M.; Sashiwa, H.; Shigemasa, Y. J. Org. Chem. 1996, 61, 6768. https://doi.org/10.1021/jo961352k

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