Bulletin of the Korean Chemical Society

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Highly Efficient Synthesis of (+)-Bromoxone, (+)-Epiepoxydon and (+)-Epiepoformin

  • Jin, Ming-Yu (Department of Chemistry, Sungkyunkwan University) ;
  • Hwang, Geum-Sook (Graduate School of Analytical Science and Technology Chungnam National University and Korea Basic Science Institute) ;
  • Chae, Hee-Il (Department of Chemistry, Sungkyunkwan University) ;
  • Jung, Sun-Hee (Department of Chemistry, Sungkyunkwan University) ;
  • Ryu, Do-Hyun (Department of Chemistry, Sungkyunkwan University)
  • Published : 2010.03.20
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References

  1. Marco-Contelles, J.; Molina, M. T.; Anjum,S. Chem. Rev. 2004, 104, 2857. https://doi.org/10.1021/cr980013j
  2. Shoji, M.; Hayashi, Y. Eur. J. Org. Chem. 2007, 3783.
  3. Ogasawara, K. J. Synth. Org. Chem. Jpn. 1999, 57, 957. https://doi.org/10.5059/yukigoseikyokaishi.57.957
  4. Gautier, E. C. L.; Lewis, N. J.; McKillop, A.; Taylor, R. J. K. Tetrahedron Lett. 1994, 35, 8759. https://doi.org/10.1016/S0040-4039(00)78490-5
  5. Johnson, C. R.; Miller, M.W. J. Org. Chem. 1995, 60, 6674. https://doi.org/10.1021/jo00126a012
  6. Adelt, S.; Plettenburg, O.;Stricker, R.; Reiser, G.; Altenbach, H.-J.; Vogel, G. J. Med. Chem.1999, 42, 1262. https://doi.org/10.1021/jm981113k
  7. Altenbach, H.-J. In Antibiotics and Antiviral Compounds; Krohn, K., Kirst, H., Maas, H., Eds.; VCH: Weinheim, 1993; pp 359-372.
  8. Block, O.; Klein, G.; Altenbach, H.-J.;Brauer, D. J. J. Org. Chem. 2000, 65, 716. https://doi.org/10.1021/jo991324c
  9. Tachihara, T.; Kitahara,T. Tetrahedron 2003, 59, 1773. https://doi.org/10.1016/S0040-4020(03)00119-4
  10. Barros, M. T.; Matias,P. M.; Maycock, C. D.; Ventura, M. R. Org. Lett. 2003, 5, 4321. https://doi.org/10.1021/ol035576i
  11. Ichihara, A.; Kimura, R.; Oda, K.; Sakamura, S. Tetrahedron Lett. 1976, 17, 4741. https://doi.org/10.1016/S0040-4039(00)93014-4
  12. Teh-Wei Chou, D.; Ganem, B. J. Am. Chem. Soc. 1980, 102, 7987. https://doi.org/10.1021/ja00547a052
  13. Ichihara, A.; Kimura, R.; Oda, K.;Moriyasu, K.; Sakamura, S. Agric. Biol. Chem. 1982, 46, 1879. https://doi.org/10.1271/bbb1961.46.1879
  14. Ichihara, A. Synthesis 1987, 207.
  15. Nagata, T.; Ando, Y.;Hiroto, A. Biosci. Biotechnol. Biochem. 1992, 56, 810. https://doi.org/10.1271/bbb.56.810
  16. Kamikubo,T.; Hiroya, K.; Ogasawara, K. Tetrahedron Lett. 1996, 37,499. https://doi.org/10.1016/0040-4039(95)02190-6
  17. Genski, T.; Taylor, R. J. K. Tetrahedron Lett. 2002, 43,3573. https://doi.org/10.1016/S0040-4039(02)00529-4
  18. Mehta, G.; Ramesh, S. S. Tetrahedron Lett. 2004, 45,1985. https://doi.org/10.1016/j.tetlet.2003.12.149
  19. Mehta, G.; Pujar, S. R.; Ramesh, S. S.; Islam, K. Tetrahedron Lett. 2005, 46, 3373. https://doi.org/10.1016/j.tetlet.2005.03.087
  20. Kamikubo, T.; Ogasawara, K. Tetrahedron Lett. 1995, 36, 1685. https://doi.org/10.1016/0040-4039(95)00131-U
  21. Barros, M. T.; Maycock, C. D.; Ventura, M. R. Chem. Eur. J.2000, 6, 3991. https://doi.org/10.1002/1521-3765(20001103)6:21<3991::AID-CHEM3991>3.3.CO;2-M
  22. Shimizu, H.; Okamura, H.; Yamashita, N.; Iwagawa,T.; Nakatani, M. Tetrahedron Lett. 2001, 42, 8649. https://doi.org/10.1016/S0040-4039(01)01871-8
  23. Carreno, M. C.; Merino, E.; Ribagorda, M.; Somoza, A.; Urbano,A. Org. Lett. 2005, 7, 1419. https://doi.org/10.1021/ol050287a
  24. Higa, T.; Okuda, R. K.; Severns, R. M.; Scheuer, P. J.; He, C-H.;Changfu, X.; Clardy, J. Tetrahedron 1987, 43, 1063. https://doi.org/10.1016/S0040-4020(01)90042-0
  25. Li, J.; Park, S.; Miller, R. L.; Lee, D. Org. Lett. 2009, 11, 4290. https://doi.org/10.1021/ol9016657
  26. Moses, J. E.; Commeiras, L.; Baldwin, J. K.; Adlington, R.M. Org. Lett. 2003, 5, 2987. https://doi.org/10.1021/ol0349817
  27. Mehta, G.; Islam, K. Tetrahedron Lett. 2004, 45, 7683. https://doi.org/10.1016/j.tetlet.2004.08.104
  28. Matsuzawa, M.; Kakeya, H.; Yamaguchi,J.; Shoji, M.; Onose, R.; Osada, H.; Hayashi, Y. Chem. Asian J.2006, 1, 845. https://doi.org/10.1002/asia.200600199
  29. Porco, J. A., Jr.; Su, S.; Lei, X.; Bardhan, S.; Rychnovsky, S.D. Angew. Chem., Int. Ed. 2006, 45, 5790. https://doi.org/10.1002/anie.200602854
  30. Mehta, G.; Roy, S.Tetrahedron Lett. 2008, 49, 1458. https://doi.org/10.1016/j.tetlet.2008.01.014
  31. Corey, E. J. Angew. Chem., Int. Ed. 2009, 48, 2100. https://doi.org/10.1002/anie.200805374
  32. Senapati,B. K.; Hwang, G.-S.; Lee, S.; Ryu, D. H. Angew. Chem., Int. Ed.,2009, 48, 4398. https://doi.org/10.1002/anie.200900351
  33. Gao, L.; Hwang, G.-S.; Lee, M. Y.; Ryu, D. H. Chem. Commun. 2009, 5460.
  34. Ryu, D. H.; Zhou, G.; Corey, E. J. Org. Lett. 2005, 7, 1633. https://doi.org/10.1021/ol0503236
  35. Ryu, D. H.; Zhou, G.; Corey, E. J. J. Am. Chem. Soc. 2004, 126,8106. https://doi.org/10.1021/ja0475959
  36. Ryu, D. H.; Corey, E. J. J. Am. Chem. Soc. 2003, 125,6388. https://doi.org/10.1021/ja035393r
  37. Ryu, D. H.; Lee, T. W.; Corey, E. J. J. Am. Chem. Soc.2002, 124, 9992. https://doi.org/10.1021/ja027468h
  38. Ryu, D. H.; Kim, K. H.; Sim, J. Y.; Corey,E. J. Tetrahedron Lett. 2007, 48, 5735. https://doi.org/10.1016/j.tetlet.2007.06.097
  39. Sim, J. Y.; Hwang, G.-S.;Kim, K. H.; Ko, E. M.; Ryu, D. H. Chem. Commun. 2007, 5064.
  40. Lee, M. Y.; Kim, K. H.; Jiang, S.; Jung, Y. H.; Sim, J. Y.;Hwang, G.-S.; Ryu, D. H. Tetrahedron Lett. 2008, 49, 1965. https://doi.org/10.1016/j.tetlet.2008.01.108
  41. Kim, J. Y.; Hwang, G.-S.; Lee, S. M.; Han, J. H.; Kim, E. Y.; Ryu,D. H. Bull. Korean Chem. Soc. 2009, 30, 289. https://doi.org/10.5012/bkcs.2009.30.2.289

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