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Concise Synthesis of Biologically Interesting Mollugin and Its Analogues

  • Lee, Yong-Rok (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Wang, Xue (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Kim, Yun-Mi (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Shim, Jae-Jin (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Kim, Byung-Nam (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Han, Do-Hung (School of Chemical Engineering and Technology, Yeungnam University)
  • Published : 2007.10.20

Abstract

The synthesis of naturally occurring mollugin and its analogues, 3,4-dihydromollugin, cis-3,4-dihydroxy-3,4- dihydromollugin, and trans-3,4-dihydroxy-3,4-dihydromollugin was achieved starting from 1,4-dihydroxynaphthalene- 2-carboxylic acid. The key reaction is an electrocyclization for pyranyl ring formation in the presence of PhB(OH)2/AcOH.

Keywords

References

  1. Singh, R.; Geetanijali; Chauhan, S. M. S. Chem. Biodiversity 2004, 1, 1241 https://doi.org/10.1002/cbdv.200490088
  2. Costa, S. M. O.; Lemos, T. L. G.; Pessoa, O. D. L.; Pessoa, C.; Montenegro, R.; Braz-Filho, R. J. Nat. Prod. 2001, 64, 792
  3. Itokawa, H.; Mihar, T.; Takeya, K. Chem. Pharm. Bull. 1983, 31, 2353 https://doi.org/10.1248/cpb.31.2353
  4. Itokawa, H.; Qiao, Y.; Takeya, K. Phytochemistry 1989, 28, 3465 https://doi.org/10.1016/0031-9422(89)80365-6
  5. Pharmacopeia of the People's Republic of China; Guangdong Science and Technology Press: Guangzhou, P. R. China, 1992; p 179
  6. Hocking, G. M. A. Dictionary of Natural Products; Plexus Publishing: Medford, NJ, 1997; p 679
  7. Inoue, K.; Shiobara, Y.; Nayeshiro, H.; Inouye, H.; Wilson, G.; Zenk, M. H. Phytochemistry 1984, 23, 307 https://doi.org/10.1016/S0031-9422(00)80323-4
  8. Kawasaki, Y.; Goda, Y.; Yoshihira, K. Chem. Pharm. Bull. 1992, 40, 1504 https://doi.org/10.1248/cpb.40.1504
  9. Marec, F.; Kollarova, I.; Jegorov, A. Planta Med. 2001, 67, 127 https://doi.org/10.1055/s-2001-11498
  10. Gutpa, P. P.; Srimal, R. C.; Verma, N.; Tandon, J. S. Pharm. Biol. 1999, 37, 46 https://doi.org/10.1076/phbi.37.1.46.6322
  11. Jpn. Kokai Tokkyo Koho, JP 08113536, 1996
  12. Ho, L.-K.; Don, M.-J.; Chen, H.-C.; Yeh, S.-F.; Chen, J.-M. J. Nat. Prod. 1996, 59, 330
  13. Chang, L. C.; Chavez, D.; Gills, J. J.; Fong, H. H. S.; Pezzuto, J. M.; Kinghorn, D. Tetrahedron Lett. 2000, 41, 7157 https://doi.org/10.1016/S0040-4039(00)01205-3
  14. Chung, M. I.; Jou, S. J.; Cheng, H. C.; Lin, C. N.; Ko, F. N.; Teng, C. M. J. Nat. Prod. 1994, 57, 313 https://doi.org/10.1021/np50104a020
  15. El-hady, S.; Bukuru, J.; Kesteleyn, B.; Kesteleyn, B.; Puyvelde, L. V.; Van, T. N.; Kimpe, N. D. J. Nat. Prod. 2002, 65, 1377 https://doi.org/10.1021/np020110e
  16. In Flore du Rwanda, Spermatophytes; Troupin, C. G., Ed.; Institu National de Recherche Scientifique: Butare (Rwanda), 1985: Vol. 3, p 196
  17. Kokwaro, J. O. Medicinal Plants of East Africa; East African Literature Bureau: Kampala, Nairobi, Dar es Salaam, 1976; p 190
  18. Van Puyvelde, L.; Geysen, D.; Ayobangira, F.-X.; Hakizamungu, E.; Nshimymana, A.; Kalisa, A. J. Ethnopharmacol. 1985, 13, 209
  19. Lee, Y. R.; Kweon, H. I.; Koh, W. S.; Min, K. R.; Kim, Y.; Lee, S. H. Synthesis 2001, 1851
  20. Lee, Y. R.; Choi, J. H.; Yoon, S. H. Tetrahedron Lett. 2005, 46, 7539 https://doi.org/10.1016/j.tetlet.2005.08.159
  21. Lee, Y. R.; Kim, D. H. Synthesis 2006, 603
  22. Lee, Y. R.; Choi, J. H.; Trinh, D. T. L.; Kim, N. W. Synthesis 2005, 3026
  23. Lee, Y. R.; Lee, W. K.; Noh, S. K.; Lyoo, W. S. Synthesis 2006, 853
  24. Lee, Y. R.; Wang, X. Bull. Korean Chem. Soc. 2005, 26, 1933 https://doi.org/10.5012/bkcs.2005.26.12.1933
  25. Lee, Y. R.; Xia, L. Bull. Korean Chem. Soc. 2007, 28, 1585 https://doi.org/10.5012/bkcs.2007.28.9.1585
  26. Schildknecht, H.; Straub, F. Liebigs Ann. Chem. 1976, 1307
  27. Ho, L.-K.; Yu, H.-J.; Ho, C.-T.; Don, M.-J. J. Chin. Chem. Soc. 2001, 48, 77
  28. Trauner, D.; Lumb, J.-P. Org. Lett. 2005, 7, 5865 https://doi.org/10.1021/ol052472u
  29. Claessens, S.; Kesteleyn, B.; Van, T. N.; De Kimpe, N. Tetrahedron 2006, 62, 8419 https://doi.org/10.1016/j.tet.2006.06.014
  30. Habonimana, P.; Claessens, S.; De Kimpe, N. Synlett 2006, 2472
  31. Pettigrew, J.; Wilson, P. D. J. Org. Chem. 2006, 71, 1620 https://doi.org/10.1021/jo052371+
  32. Chauder, B. A.; Lopes, C. C.; Lopes, R. S. C.; Da Silva, A. J. M.; Snieckus, V. Synthesis 1998, 279
  33. Bal-Tembe, S.; Bhedi, D. N.; de Souza, N. J.; Rupp, R. H. Heterocycles 1987, 26, 1239
  34. Kwueon, E. K.; Choi, D. S.; Choi, H. Y.; Lee, Y. J.; Jo, C. H.; Hwang, S. H.; Park, Y. S.; Song, C. E. Bull. Korean Chem. Soc. 2005, 26, 1839 https://doi.org/10.5012/bkcs.2005.26.11.1839

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