Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Stereoselective Syntheses of 3-Substituted Flavene Derivatives and Asymmetric Dehydration via Kinetic Resolution

  • Lee, Min-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, Yoon-Min (Department of Chemistry and Bio/Molecular Informatics Center, Konkuk University) ;
  • Kim, Da-Jung (Department of Chemistry and Bio/Molecular Informatics Center, Konkuk University) ;
  • Park, Yong-Sun (Department of Chemistry and Bio/Molecular Informatics Center, Konkuk University)
  • Published : 2008.07.20
Download PDF
⟨ Previous Next ⟩

Abstract

Keywords

References

  1. Satoh, Y.; Stanton, J. L.; Hutchison, A. J.; Libby, A. H.; Kowalski, T. J.; Lee, W. H.; White, D. H.; Kimble, E. F. J. Med. Chem. 1993, 36, 3580 https://doi.org/10.1021/jm00075a013
  2. Cheng, J.-F.; Ishikawa, A.; Ono, Y.; Arrhenius, T.; Nadzan, A. Bioorg. Med. Chem. Lett. 2003, 13, 3647 https://doi.org/10.1016/j.bmcl.2003.08.025
  3. Hajela, K.; Pandey, J.; Dwivedy, A.; Dhar, J. D.; Sarkhel, S.; Maulik, P. R.; Velumurugan, D. Bioorg. Med. Chem. 1999, 7, 2083 https://doi.org/10.1016/S0968-0896(99)00131-5
  4. Ishizuka, N.; Matsumura, K.-i.; Kikuchi, J.; Nakai, H. Bioorg. Med. Chem. 2002, 10, 3965 https://doi.org/10.1016/S0968-0896(02)00300-0
  5. Funk, O. F.; Kettmann, V.; Drimal, J.; Langer, T. J. Med. Chem. 2004, 47, 2750 https://doi.org/10.1021/jm031041j
  6. Ishizuka, N.; Matsumura, K.-i.; Sakai, K.; Fujimoto, M.; Mihara, S.-i.; Yamamori, T. J. Med. Chem. 2002, 45, 2041 https://doi.org/10.1021/jm010382z
  7. Sunden, H.; Ibrahem, I.; Zhao, G.-L.; Eriksson, L.; Cordova, A. Chem. Eur. J. 2007, 13, 574 https://doi.org/10.1002/chem.200600572
  8. Li, H.; Wang, J.; E-Nunu, T.; Zu, L.; Jiang, W.; Wei, S.; Wang, W. Chem. Commun. 2007, 507
  9. Govender, T.; Hojabri, L.; Moghaddam, F. M.; Arvidsson, P. I. Tetrahedron: Asymmetry 2006, 17, 1763 https://doi.org/10.1016/j.tetasy.2006.06.028
  10. Konoike, T.; Matsumura, K.-i.; Yorifuji, T.; Shinomoto, S.; Ide, Y.; Ohya, T. J. Org. Chem. 2002, 67, 7741 https://doi.org/10.1021/jo0261092
  11. Hardouin, C.; Burgaud, L.; Valleix, A.; Doris, E. Tetrahedron Lett. 2003, 44, 435 https://doi.org/10.1016/S0040-4039(02)02614-X
  12. Robinson, D. E. J. E.; Bull, S. D. Tetrahedron: Asymmetry 2003, 14, 1407 https://doi.org/10.1016/S0957-4166(03)00209-X
  13. Keith, J. M.; Larrow, J. F.; Jacobson, E. N. Adv. Synth. Catal. 2001, 343, 5 https://doi.org/10.1002/1615-4169(20010129)343:1<5::AID-ADSC5>3.0.CO;2-I
  14. Vedejs, E.; Daugulis, O. J. Am. Chem. Soc. 2003, 125, 4166 https://doi.org/10.1021/ja021224f
  15. Tao, B.; Ruble, J. C.; Hoic, D. A.; Fu, G. C. J. Am. Chem. Soc. 1999, 121, 5091 https://doi.org/10.1021/ja9906958
  16. Miller, S. J.; Copeland, G. T.; Papaioannou, N.; Horstmann, T. E.; Ruel, E. M. J. Am. Chem. Soc. 1998, 120, 1629 https://doi.org/10.1021/ja973892k
  17. Mazet, C.; Roseblade, S.; Köhler, V.; Pfaltz, A. Org. Lett. 2006, 8, 1879 https://doi.org/10.1021/ol060443t
  18. Yamada, S.; Misono, T.; Iwai, Y. Tetrahedron Lett. 2005, 46, 2239 https://doi.org/10.1016/j.tetlet.2005.02.019
  19. Suzuki, Y.; Yamauchi, K.; Muramatsu, K.; Sato, M. Chem. Commun. 2004, 2770
  20. Kim, Y.; Choi, E. T.; Lee, M. H.; Park, Y. S. Tetrahedron Lett. 2007, 48, 2833 https://doi.org/10.1016/j.tetlet.2007.02.111
  21. Choi, E. T.; Lee, M. H.; Kim, Y.; Park, Y. S. Tetrahedron 2008, 64, 1515 https://doi.org/10.1016/j.tet.2007.11.026

Cited by

  1. Bioactive Phytochemicals: Efficient Synthesis of Optically Active Substituted Flav-3-enes and Flav-3-en-3-o-R Derivatives vol.2017, pp.2090-9071, 2017, https://doi.org/10.1155/2017/3971253
  2. ChemInform Abstract: Stereoselective Syntheses of 3-Substituted Flavene Derivatives and Asymmetric Dehydration via Kinetic Resolution. vol.39, pp.46, 2008, https://doi.org/10.1002/chin.200846138
  3. Kinetic Resolution of β-Alkenyl-, β-Alkynyl- and β-Flavenyl-Substituted β-Hydroxy Esters in Asymmetric Dehydration vol.2008, pp.33, 2008, https://doi.org/10.1002/ejoc.200800807
  4. Kinetic Resolution of β-Chromenyl-β-Hydroxy Esters for Asymmetric Preparation of Flavene Derivatives vol.30, pp.5, 2008, https://doi.org/10.5012/bkcs.2009.30.5.1211