DOI QR코드

DOI QR Code

A New Synthetic Route for Natural Products with the Pyranobenzophenone Moiety: Clusiacitran A, Vismiaphenone B, Isovismiaphenone B, and Myrtiaphenone B

  • Lee, Yong-Rok (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Kim, Jung-Hee (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Yong, Chul-Soon (College of Pharmacy, Yeungnam University) ;
  • Im, Jong-Sub (College of Pharmacy, Yeungnam University) ;
  • Lyoo, Won-Seok (School of Textiles, Yeungnam University)
  • Published : 2008.02.20

Abstract

Keywords

References

  1. Bernardi, A. P. M.; Ferraz, A. B. F.; Albring, D. V.; Bordignon, A. A. L.; Schripsema, J.; Bridi, R.; Dutra-Filho, C. S.; Henriques, A. T.; von Poser, G. L. J. Nat. Prod. 2005, 68, 784 https://doi.org/10.1021/np040149e
  2. McKee, T. C.; Covington, C. D.; Fuller, R. W.; Bokesch, H. R.; Young, S.; Cardellina, J. H., II; Kadushin, M. R.; Soejarto, D. D.; Stevens, P. F.; Cragg, G. M.; Boyd, M. R. J. Nat. Prod. 1998, 61, 1252 https://doi.org/10.1021/np980140a
  3. Cao, S.-G.; Wu, X.-H.; Sim, K.-Y.; Tan, B. H. K.; Vittal, J. J.; Pereira, J. T.; Goh, S.-H. Helv. Chim. Acta 1998, 81, 1404 https://doi.org/10.1002/hlca.19980810549
  4. Cao, S.-G.; Sim, K.-Y.; Pereira, J.; Goh, S.-H. Phytochemistry 1998, 47, 1051 https://doi.org/10.1016/S0031-9422(97)00643-2
  5. Cao, S. G.; Chong, K. L.; Vittal, J. J.; Sim, K. Y.; Goh, S. H. Nat. Prod. Lett. 1998, 11, 233 https://doi.org/10.1080/10575639808044952
  6. Gustafson, K. R.; Bokesch, H. R.; Fuller, R. W.; Cardellina, J. H., II; Kadushin, M. R.; Soejarto, D. D.; Boyd, M. R. Tetrahedron Lett. 1994, 35, 5821 https://doi.org/10.1016/S0040-4039(00)78193-7
  7. Ito, C.; Itoigawa, M.; Mishina, Y.; Filho, V. C.; Enjo, F.; Tokuda, H.; Nishino, H.; Furukawa, H. J. Nat. Prod. 2003, 66, 368 https://doi.org/10.1021/np0203640
  8. Fuller, R. W.; Blunt, J. W.; Boswell, J. L.; Cardellina, J. H., II; Boyd, M. R. J. Nat. Prod. 1999, 62, 130 https://doi.org/10.1021/np9801514
  9. Fuller, R. W.; Westergaard, C. K.; Collins, J. W.; Cardellina, J. H., II; Boyd, M. R. J. Nat. Prod. 1999, 62, 67 https://doi.org/10.1021/np980152w
  10. Chaturvedula, V. S. P.; Schilling, J. K.; Kingston, D. G. I. J. Nat. Prod. 2002, 65, 965 https://doi.org/10.1021/np020030a
  11. Prado, S.; janin, Y. L.; Saint-Joanis, B.; Brodin, P.; Michel, S.; Koch, M.; Cole, S. T.; Tillequin, F.; Bost, P.-E. Bioorg. Med. Chem. 2007, 15, 2177 https://doi.org/10.1016/j.bmc.2006.12.009
  12. Gonzalez, J. G.; Olivares, E. M.; Monache, F. D. Phytochemistry 1995, 38, 485 https://doi.org/10.1016/0031-9422(94)00642-7
  13. Fun, H.-K.; Kysomboon, S.; Chantrapromma, K.; Chantrapromma, S. Acta Crrst. 2006, E62, o3228
  14. Monache, G. D.; Gonzalez, J. G.; Monache, F. D.; Bettolo, G. B. M. Phytochemistry 1980, 19, 2025 https://doi.org/10.1016/0031-9422(80)83030-5
  15. Gonzalez, J. G.; Cuellar, V.; Betancourt, A.; Pinzon, M. I. Phytochemistry 1983, 22, 2088 https://doi.org/10.1016/0031-9422(83)80055-7
  16. Pathak, V. P.; Khanna, R. N. Bull. Chem. Soc. Jpn. 1982, 55, 2264 https://doi.org/10.1246/bcsj.55.2264
  17. Spino, C.; Lal, J.; Sotheeswaran, S.; Aalbersberg, W. Phytochemistry 1995, 38, 233 https://doi.org/10.1016/0031-9422(94)00589-L
  18. Ali, S.; Goundar, R.; Sotheeswaran, S.; Beaulier, C.; Spino, C. Phytochemistry 2000, 53, 281 https://doi.org/10.1016/S0031-9422(99)00511-7
  19. Lee, Y. R.; Kim, J. H. Synlett 2007, 2232
  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.; Wang, X. Bull. Korean Chem. Soc. 2005, 26, 1933 https://doi.org/10.5012/bkcs.2005.26.12.1933
  22. Lee, Y. R.; Xia, L. Bull. Korean Chem. Soc. 2007, 28, 1585
  23. Wang, X.; Lee, Y. R. Synthesis 2007, 3044
  24. Lee, Y. R.; Xia, X. Synthesis 2007, 3244
  25. Wang, X.; Lee, Y. R. Tetrahedron Lett. 2007, 48, 6275 https://doi.org/10.1016/j.tetlet.2007.07.022
  26. Lee, Y. R.; Li, X. Bull. Korean Chem. Soc. 2007, 28, 1739 https://doi.org/10.5012/bkcs.2007.28.10.1739
  27. Lin, C.-M.; Huang, S.-T.; Lee, F.-W.; Kuo, H.-S.; Lin, M.-H. Bioorg. Med. Chem. 2006, 14, 4402 https://doi.org/10.1016/j.bmc.2006.02.042
  28. Calderon-Higginson, C.; Crombie, L.; Redshaw, S. D.; Whiting D. A. J. Chem. Soc., Perkin Trans. 1 2000, 2491
  29. Shoyama, Y.; Morimoto, S.; Nishioka, I. Chem. Pharm. Bull. 1981, 29, 3720 https://doi.org/10.1248/cpb.29.3720
  30. Wu, T.-S.; Wang, M.-L.; Wu, P.-L.; Jong, T.-T. Phytochemistry 1995, 40, 1817 https://doi.org/10.1016/0031-9422(95)00447-F
  31. Wu, T.-S.; Wang, M.-L.; Wu, P.-L. Phytochemistry 1996, 43, 785 https://doi.org/10.1016/0031-9422(96)00361-5

Cited by

  1. Total Syntheses of Cannabicyclol, Clusiacyclol A and B, Iso-Eriobrucinol A and B, and Eriobrucinol vol.15, pp.12, 2013, https://doi.org/10.1021/ol401335u
  2. Synthesis of 3-geranyl- and 3-prenyl-2,4,6-trihydroxybenzophenone vol.47, pp.6, 2017, https://doi.org/10.1080/00397911.2016.1276603
  3. ChemInform Abstract: A New Synthetic Route for Natural Products with the Pyranobenzophenone Moiety: Clusiacitran A (XIII), Vismiaphenone B (VII), Isovismiaphenone B (VIII), and Myrtiaphenone B (X). vol.39, pp.28, 2008, https://doi.org/10.1002/chin.200828197
  4. Phloroglucinol compounds of natural origin: Synthetic aspects vol.27, pp.3, 2010, https://doi.org/10.1039/b914364p
  5. Synthesis of fluorine-containing prenylated benzophenones vol.50, pp.14, 2008, https://doi.org/10.1080/00397911.2020.1771597