DOI QR코드

DOI QR Code

An Efficient and Concise Synthesis of Biologically Interesting Natural Flemichapparin A, Flemingin A, Flemingin D, and Their Non-natural Analogues

  • Lee, Yong-Rok (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Xia, Likai (School of Chemical Engineering and Technology, Yeungnam University)
  • Published : 2007.09.20

Abstract

The efficient and concise synthesis of natural and non-natural pyranochalcones was achieved from readily available 2,4,5-trihydroxyacetophenone. The key steps in the synthetic strategy were ethylenediamine diacetate-catalyzed benzopyran formation and aldol 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., Ed.; 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. Magalhaes, A. F.; Azevedo Tozzi, A. M. G.; Noronha Sales, B. H. L.; Magalhaes, E. G. Phytochemistry 1996, 42, 1459 https://doi.org/10.1016/0031-9422(96)00134-3
  10. Fang, N.; Casida, J. E. J. Nat. Prod. 1999, 62, 205 https://doi.org/10.1021/np980119+
  11. Saini, T. R.; Pathak, V. P.; Khanna, R. N. J. Nat. Prod. 1983, 46, 936
  12. Pathak, V. P.; Saini, T. R.; Khanna, R. N. Phytochemistry 1983, 22, 1303 https://doi.org/10.1016/0031-9422(83)80254-4
  13. Subrahmanyam, K.; Madhusudhana Rao, V.; Jagannadha Rao, K. V. Indian J. Chem. 1997, 15B, 12
  14. 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: Biochemical, Pharmacological and Structure-Activity Relationship; Cody, V., Middleton, E., Jr., Harborne, J. B., Eds.; Alan R. Liss, Inc.: New York, 1986; p 231
  15. 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
  16. Han, A.-R.; Kang, Y.-J.; Windono, T.; Lee, S. K.; Seo, E.-K. J. Nat. Chem. 2006, 69, 719
  17. 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
  18. Adityachaudhury, N.; Ghosh, D.; Choudhury, A.; Kirtaniya, C. L. J. Indian Chemical. Soc. 1973, 50, 363
  19. Chowdhury, A.; Mukherjee, N.; Adityachaudhury, N. Experientia 1974, 30, 1022 https://doi.org/10.1007/BF01938986
  20. Cardillo, G.; Merlini, L.; Mondelli, L. Tetrahedron 1968, 24, 497 https://doi.org/10.1016/0040-4020(68)89049-0
  21. Pavolini, T.; Gambarin, F. Agrochimica 1957, 2, 88
  22. Cardillo, B.; Gennaro, A.; Merlini, L.; Nasini, G.; Servi, S. Phytochemistry 1973, 12, 2027 https://doi.org/10.1016/S0031-9422(00)91528-0
  23. Iyer, M. R.; Trivedi, G. K. J. Nat. Prod. 1993, 56, 268 https://doi.org/10.1021/np50092a012
  24. Adityachaudhury, N.; Chowdhury, A.; Kirtaniya, C.; Chatterjee, A. Chemistry & Industry 1975, 179
  25. Yamada, S.; Ono, F.; Katagiri, T.; Tanaka, J. Bull. Chem. Soc. Jpn. 1975, 48, 2391 https://doi.org/10.1246/bcsj.48.2391
  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.; Wang, X. Bull. Korean Chem. Soc. 2005, 26, 1933 https://doi.org/10.5012/bkcs.2005.26.12.1933
  28. Cardillo, G.; Merlini, L.; Mondelli, R. Tetrahedron Lett. 1970, 4367

Cited by

  1. ]chromen-6-yl)ethanone vol.68, pp.10, 2012, https://doi.org/10.1107/S160053681204055X
  2. ChemInform Abstract: An Efficient and Concise Synthesis of Biologically Interesting Natural Flemichapparin A (Ia), Flemingin A (If), Flemingin D (Ie), and Their Non-Natural Analogues. vol.39, pp.8, 2008, https://doi.org/10.1002/chin.200808217
  3. First Concise Total Syntheses of Biologically Interesting Nicolaioidesin C, Crinatusin C1, and Crinatusin C2 vol.29, pp.6, 2007, https://doi.org/10.5012/bkcs.2008.29.6.1199
  4. Concise Total Synthesis of Biologically Interesting Prenylated Chalcone Natural Products: 4'-O-Methylxanthohumol, Xanthohumol E, and Sericone vol.29, pp.6, 2007, https://doi.org/10.5012/bkcs.2008.29.6.1205