Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of Versatile 1-Indanones and their Conversion to 1,2-Naphthoquinones, Key Precursors for the Construction of Perylenequinone Core

  • Hwang, Ki-Jun (Research Center of Bioactive Materials, Chonbuk National University) ;
  • Shin, Young-Min (Department of Chemistry, Chonbuk National University) ;
  • Kim, Dae-Hyuk (Department of Molecular Biology, Chonbuk National University) ;
  • Kim, Beom-Tae (Research Center of Bioactive Materials, Chonbuk National University)
  • Received : 2012.05.16
  • Accepted : 2012.05.31
  • Published : 2012.09.20
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References

  1. Weiss, U.; Nasini, G. Prog. Chem. Org. Nat. Prod. 1987, 52, 1.
  2. Diwu, Z. J.; Lown, J. W. Photochem. Photobiol. 1990, 52, 609-616. https://doi.org/10.1111/j.1751-1097.1990.tb01807.x
  3. Lown, J. W. Can. J. Chem. 1997, 75, 99-119. https://doi.org/10.1139/v97-015
  4. Diwu, Z. J. Photochem. Photobiol. 1995, 61, 529-539. https://doi.org/10.1111/j.1751-1097.1995.tb09903.x
  5. Falk, H. Angew. Chem. Int. Ed. 1999, 38, 3116-3136. https://doi.org/10.1002/(SICI)1521-3773(19991102)38:21<3116::AID-ANIE3116>3.0.CO;2-S
  6. Kobayashi, E.; Nakano, H.; Morimoto, M.; Tamaoki, T. Biochem. Biophys. Res. Commun. 1989, 159, 548-553. https://doi.org/10.1016/0006-291X(89)90028-4
  7. Nishizuka, Y. Cancer 1989, 63, 1892-1903. https://doi.org/10.1002/1097-0142(19890515)63:10<1892::AID-CNCR2820631005>3.0.CO;2-Z
  8. Hinterding, K.; Alonso-Diaz, D.; Waldmann, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 689-749.
  9. Kobayashi, E.; Nakano, H.; Morimoto, M.; Tamaoki, T. Biochem. Biophys. Res. Commun. 1989, 159, 548-553. https://doi.org/10.1016/0006-291X(89)90028-4
  10. Nishizuka, Y. Cancer 1989, 63, 1892-1903. https://doi.org/10.1002/1097-0142(19890515)63:10<1892::AID-CNCR2820631005>3.0.CO;2-Z
  11. Hinterding, K.; Alongso-Diaz, D.; Waldmann, H. Angew. Chem., Int. Ed. Engl. 1998, 37, 689-749.
  12. Beck, T. P.; Kirsh, E. J.; Chmura, S. J.; Kovar, D. A.; Chung, T.; Rinker-Schaefer, C. W.; Stadler, W. M. Urology 1999, 54, 573-577. https://doi.org/10.1016/S0090-4295(99)00210-1
  13. Pollack, I. F.; Kawecki, S. J. Neuro-Oncol. 1997, 31, 255-266. https://doi.org/10.1023/A:1005729626354
  14. Dubauskas, Z.; Beck, T. P.; Chmura, S. J.; Kovar, D. A.; Kadkhodaian, M. M.; Shrivastav, M.; Chung, T.; Stadler, W. M.; Rinker-Schaefer, C. W. Clin. Can. Res. 1998, 4, 2391- 2398.
  15. Zhu, D.-M.; Narla, R.-K.; Fang, W.-H.; Chia, N.-C.; Uckun, F. M. Clin. Can. Res. 1998, 4, 2967-2976.
  16. Xing, M.-Z.; Zhang, X.-Z.; Sun, Z.-L.; Zhang, H. Y. J. Agric. Food Chem. 2003, 51, 7722-7724. https://doi.org/10.1021/jf0348774
  17. Broka, C. A. Tetrahedron Lett. 1991, 32, 859-862. https://doi.org/10.1016/S0040-4039(00)92105-1
  18. Coleman, R. S.; Grant, E. B. J. Am. Chem. Soc. 1995, 117, 10889-10904. https://doi.org/10.1021/ja00149a012
  19. Coleman, R. S.; Grant, E. B. J. Am. Chem. Soc. 1994, 116, 8795-8796. https://doi.org/10.1021/ja00098a043
  20. Coleman, R. S.; Grant, E. B. Tetrahedron Lett. 1993, 34, 2225. https://doi.org/10.1016/S0040-4039(00)77579-4
  21. Coleman, R. S.; Grant, E. B. J. Org. Chem. 1991, 56, 1357-1359. https://doi.org/10.1021/jo00004a006
  22. Merlic, C. A.; Aldrich, C. C.; Albaneze-Walker, J.; Saghatelian, A. J. Am. Chem. Soc. 2000, 122, 3224-3225. https://doi.org/10.1021/ja994313+
  23. Merlic, C. A.; Aldrich, C. C.; Albaneze-Walker, J.; Saghatelian, A.; Mammen, J. J. Org. Chem. 2001, 66, 1297-1309. https://doi.org/10.1021/jo0014663
  24. Liu, J.; Diwu, Z.; Lown, J. W. Synthesis 1995, 914-916.
  25. Hauser, F. M.; Sengupta, D.; Corlett, S. A. J. Org. Chem. 1994, 59, 1967-1969. https://doi.org/10.1021/jo00087a006
  26. Diwu, Z.; Lown, J. W. Tetrahedron 1992, 48, 45-54. https://doi.org/10.1016/S0040-4020(01)80577-9
  27. Zhao, C.; Zhang, X.-S.; Zhang, P. Liebigs Ann. Chem. 1993, 35-41.
  28. Chao, C.; Zhang, P. Tetrahedron Lett. 1988, 29, 225-226. https://doi.org/10.1016/S0040-4039(00)80060-X
  29. Liu, J.; Diwu, Z.; Lown, J. W. Tetrahedron 1993, 49, 10785-10792. https://doi.org/10.1016/S0040-4020(01)80233-7
  30. Kim, B.-T.; Kim, H.-S.; Moon, W. S.; Hwang, K.-J. Tetrahedron 2009, 65, 4625-4628. https://doi.org/10.1016/j.tet.2009.03.057
  31. Cui, D.-M.; Zhang, C.; Kawamura, M.; Shinmada, S. Tetrahedron Lett. 2004, 45, 1741-1745.
  32. Olah, G. A.; Mathew, T.; Farnia, M.; Prakash, G. K. S. Synlett. 1999, 1067-1068.
  33. Shintani, R.; Okamoto, K.; Hayashi, T. J. Am. Chem. Soc. 2005, 127, 2872-2873. https://doi.org/10.1021/ja042582g
  34. Shintani, R.; Hayashi, T. Org. Lett. 2005, 7, 2071-2073. https://doi.org/10.1021/ol0506819
  35. Kundu, K.; McCullagh, J. V.; Morehead, A. T., Jr. J. Am. Chem. Soc. 2005, 127, 16042-16043. https://doi.org/10.1021/ja0564416
  36. Gagnier, S. V.; Larock, R. C. J. Am. Chem. Soc. 2003, 125, 4804-4807. https://doi.org/10.1021/ja0212009
  37. Spoerri, P. E.; DuBois, A. S. Org. React. 1949, 5, 387-412.
  38. Sato, Y.; Yato, M.; Ohwada, T.; Saito, S.; Shudo, K. J. Am. Chem. Soc. 1995, 117, 3037-3043. https://doi.org/10.1021/ja00116a009
  39. Nakamura, S.; Sugimoto, H.; Ohwada, T. J. Org. Chem. 2008, 73, 4219-4224. https://doi.org/10.1021/jo800674h
  40. Iwaya, K.; Nakamura, M.; Hasegawa, E. Tetrahedron Lett. 2002, 43, 5067-5070. https://doi.org/10.1016/S0040-4039(02)01007-9
  41. Liu, Y.; Zhang, Y. Tetrahedron Lett. 2001, 42, 5745-5748. https://doi.org/10.1016/S0040-4039(01)01107-8

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