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Concise Synthetic Approaches to Naturally Occurring β-Hydroxypyranochalcones: First Total Synthesis of Purpurenone, Its Derivative, and Praecansone B

  • Wang, Xue (School of Chemical Engineering, Yeungnam University) ;
  • Lee, Yong-Rok (School of Chemical Engineering, Yeungnam University) ;
  • Kim, Sung-Hong (Analysis Research Division, Daegu Center, Korea Basic Science Institute)
  • Received : 2012.05.01
  • Accepted : 2012.05.14
  • Published : 2012.08.20

Abstract

The total synthesis of biologically interesting ${\beta}$-hydroxypyranochalcones, purpurenone (1), its derivative 2, praecansone B (3), and pongapinone A (4) has been accomplished starting from commercially available 2,4-dihydroxyacetophenone or 6-methoxy-2,4-dihydroxyacetophenone in 3 steps by a convergent strategy through benzopyran formations, O-methylations, and coupling reactions.

Keywords

References

  1. Wagner, H.; Farkas, L. In The Flavonoids; Harorne, J. B., Mabry, T. J., Mabry, H., Eds.; Academic Press: New York, 1975; p 127.
  2. Gripenberg, J. In The Chemistry of Flavonoid Compounds; Geissman, T. A., Ed.; MacMillan: New York, 1962; p 409.
  3. Wollenweber, E. In The Flavonoids; Harborne, J. B., Ed.; Chapman & Hall: London, 1994; p 259.
  4. In The Handbook of Natural Products; Harborne, J. B., Baxter, H., Eds.; John Wiley & Sons Ltd.: London, 1999; Vol 2, p 1.
  5. Fang, N.; Casida, J. E. J. Nat. Prod. 1999, 62, 205. https://doi.org/10.1021/np980119+
  6. Saini, T. R.; Pathak, V. P.; Khanna, R. N. J. Nat. Prod. 1983, 46, 936.
  7. Pathak, V. P.; Saini, T. R.; Khanna, R. N. Phytochemistry 1983, 22, 1303. https://doi.org/10.1016/0031-9422(83)80254-4
  8. Subrahmanyam, K.; Madhusudhana Rao, V.; Jagannadha Rao, K. V. Indian J. Chem. 1997, 15B, 12.
  9. Rao, M. S.; Rao, P. S.; Toth, G.; Balazs, B.; Duddeck, H. J. Nat. Prod. 1998, 61, 1148. https://doi.org/10.1021/np980043h
  10. Krohn, K.; Steingrover, K.; Rao, M. S. Phytochemistry 2002, 61, 931. https://doi.org/10.1016/S0031-9422(02)00475-2
  11. Narender, T.; Tanvir, S. K.; Rao, M. S.; Srivastava, K.; Puri, S. K. Bioorg. Med. Chem. Lett. 2005, 15, 2453. https://doi.org/10.1016/j.bmcl.2005.03.081
  12. Welton, A. F.; Tobias, L. D.; Fiedler-Nagy, C.; Anderson, W.; Hope. W.; Meyers, K.; Coffey, J. W. In Plant Flavnoids in Biology and Medicine
  13. Miranda, C. L.; Stevens, J. F.; Helmrich, A.; Henderson, M. C.; Rodriguez, R. J.; Yang, Y.-H.; Deinzer, M. L. Barnes, D. W.; Buhler, D. R. Food Chem. Toxicol. 1999, 37, 271. https://doi.org/10.1016/S0278-6915(99)00019-8
  14. Han, A.-R.; Kang, Y.-J.; Windono, T.; Lee, S. K.; Seo, E.-K. J. Nat. Chem. 2006, 69, 719.
  15. Demizu, S.; Kajiyama, K.; Hiraga, Y.; Kinoshida, T.; Koyama, K.; Takahashi, K.; Tamura, Y.; Okada, K.; Kinoshida, T. Chem. Pharm. Bull. 1992, 40, 392. https://doi.org/10.1248/cpb.40.392
  16. Narender, T.; Gupta, S.; Gupta, S. Bioorg. Med. Chem. Lett. 2004, 14, 3913. https://doi.org/10.1016/j.bmcl.2004.05.071
  17. Magalhaes, A. F.; Tozzi, A. M. G. A.; Sales, B. H. L. N.; Magalhaes, E. G. Phytochemistry 1996, 42, 1459. https://doi.org/10.1016/0031-9422(96)00134-3
  18. Magalhaes, A. F.; Tozzi, A. M. G. A.; Magalhaes, E. G.; Sannomiya, M.; Soriano, M. D. P. C.; Perez, M. A. F. An Acad. Bras. Cienc. 2007, 79, 351. https://doi.org/10.1590/S0001-37652007000300001
  19. Tarus, P. K.; Machacho, A. K.; Lang'at-Thoruwa, C. C.; Chhabra, S. C. Phytochemistry 2002, 60, 375. https://doi.org/10.1016/S0031-9422(02)00078-X
  20. Kokwaro, J. O. Medicinal Plants of East Africa; East African Literature Bureau: Nairobi, 1993; p 250.
  21. Gillet, J. B.; Polhill, R. M.; Verdcourt, B. Flora of Tropical East Africa; The Government Printers: Nairobi, 1071; p 501.
  22. Kitagawa, I.; Zhang, R.-S.; Hori, K.; Tsuchiya, K.; Shibuya, H. Chem. Pharm. Bull. 1992, 40, 2041. https://doi.org/10.1248/cpb.40.2041
  23. Nakahira, H.; Sunagawa, M. Tetrahedron Lett. 1997, 38, 4443. https://doi.org/10.1016/S0040-4039(97)00927-1
  24. Lee, Y. R.; Kim, D. H. Synthesis 2006, 603.
  25. Lee, Y. R.; Xia, L. Synthesis 2007, 3240.
  26. Lee, Y. R.; Choi, J. H.; Yoon, S. H. Tetrahedron Lett. 2005, 46, 7539. https://doi.org/10.1016/j.tetlet.2005.08.159
  27. Lee, Y. R.; Lee, W. K.; Noh, S. K.; Lyoo, W. S. Synthesis 2006, 853.
  28. Lee, Y. R.; Kim, J. H. Synlett. 2007, 2232.
  29. Wang, X.; Lee, Y. R. Tetrahedron Lett. 2007, 48, 6275. https://doi.org/10.1016/j.tetlet.2007.07.022
  30. Lee, Y. R.; Li, X.; Kim, J. H. J. Org. Chem. 2008, 73, 4313. https://doi.org/10.1021/jo800367r
  31. Hari, G. S.; Lee, Y. R. Bull. Korean Chem. Soc. 2011, 32, 2949. https://doi.org/10.5012/bkcs.2011.32.8.2949
  32. Lim, D.; Zhou, G.; Livanos, A. E.; Fang, F.; Coltart, D. M. Synthesis 2008, 2148.

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