Table of Contents
ISRN Organic Chemistry
Volume 2011, Article ID 239817, 7 pages
http://dx.doi.org/10.5402/2011/239817
Review Article

Progress in the Total Synthesis of Rocaglamide

1College of Chemistry and Environmental Science, Guizhou University for Nationalites, Guiyang 550025, China
2College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, China

Received 22 January 2011; Accepted 13 February 2011

Academic Editors: T. J. Brocksom, A. Iuliano, and N. Nishiwaki

Copyright © 2011 Xiao-hua Cai et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. P. Proksch, “Chemistry and biological activity of rocaglamide derivatives and related compounds in Aglaia species (Meliaceae),” Current Organic Chemistry, vol. 5, no. 9, pp. 923–938, 2001. View at Publisher · View at Google Scholar
  2. H. Greger, M. Hofer, K. Teichmann et al., “Amide-esters from Aglaia tenuicaulis—first representatives of a class of compounds structurally related to bisamides and flavaglines,” Phytochemistry, vol. 69, no. 4, pp. 928–938, 2008. View at Publisher · View at Google Scholar · View at Scopus
  3. S. Kim, A. A. Salim, S. M. Swanson, and A. D. Kinghorn, “Potential of cyclopenta[b]benzofurans from Aglaia species in cancer chemotherapy,” Anti-Cancer Agents in Medicinal Chemistry, vol. 6, no. 4, pp. 319–345, 2006. View at Publisher · View at Google Scholar · View at Scopus
  4. M. L. King, C. C. Chiang, H. C. Ling et al., “X-ray crystal structure of rocaglamide, a novel antileukemic 1H-cyclopenta[b]benzofuran from Aglaia elliptifolia,” Journal of the Chemical Society—Series, vol. No. 20, pp. 1150–1151, 1982. View at Google Scholar
  5. P. Proksch, M. Giaisi, M. K. Treiber et al., “Rocaglamide derivatives are immunosuppressive phytochemicals that target NF-AT activity in T cells,” Journal of Immunology, vol. 174, no. 11, pp. 7075–7084, 2005. View at Google Scholar
  6. T. S. Wu, M. J. Liou, C. S. Kuoh, C. M. Teng, T. Nagao, and K. H. Lee, “Cytotoxic and antiplatelet aggregation principles from Aglaia elliptifolia,” Journal of Natural Products, vol. 60, no. 6, pp. 606–608, 1997. View at Publisher · View at Google Scholar · View at Scopus
  7. B. Hausott, H. Greger, and B. Marian, “Flavaglines: a group of efficient growth inhibitors block cell cycle progression and induce apoptosis in colorectal cancer cells,” International Journal of Cancer, vol. 109, no. 6, pp. 933–940, 2004. View at Publisher · View at Google Scholar · View at Scopus
  8. J. Y. Zhu, I. N. Lavrik, U. Mahlknecht et al., “The traditional Chinese herbal compound rocaglamide preferentially induces apoptosis in leukemia cells by modulation of mitogen-activated protein kinase activities,” International Journal of Cancer, vol. 121, no. 8, pp. 1839–1846, 2007. View at Publisher · View at Google Scholar · View at Scopus
  9. F. Thuaud, Y. Bernard, G. Turkeri et al., “Synthetic analogue of rocaglaol displays a potent and selective cytotoxicity in cancer cells: involvement of apoptosis inducing factor and caspase-12,” Journal of Medicinal Chemistry, vol. 52, no. 16, pp. 5176–5187, 2009. View at Publisher · View at Google Scholar · View at Scopus
  10. J. Janprasert, C. Satasook, P. Sukumalanand et al., “Rocaglamide, a natural benzofuran insecticide from Aglaia odorata,” Phytochemistry, vol. 32, no. 1, pp. 67–69, 1992. View at Google Scholar · View at Scopus
  11. L. P. Molleyres, A. Rindlisbacher, T. Winkler, and V. Kumar, “Resistance to glyphosate in Lolium rigidum,” Pesticide Science, vol. 55, pp. 486–503, 1999. View at Google Scholar
  12. M. Dreyer, B. W. Nugroho, F. I. Bohnenstengel et al., “New insecticidal rocaglamide derivatives and related compounds from Aglaia oligophylla,” Journal of Natural Products, vol. 64, no. 4, pp. 415–420, 2001. View at Publisher · View at Google Scholar · View at Scopus
  13. J. Hiort, Chaidir, F. I. Bohnenstengel et al., “New insecticidal rocaglamide derivatives from the roots of Aglaia duperreana,” Journal of Natural Products, vol. 62, no. 12, pp. 1632–1635, 1999. View at Publisher · View at Google Scholar · View at Scopus
  14. B. W. Nugroho, R. A. Edrada, B. Güssregen, V. Wray, L. Witte, and P. Proksch, “Insecticidal rocaglamide derivatives from Aglaia duppereana,” Phytochemistry, vol. 44, no. 8, pp. 1455–1461, 1997. View at Publisher · View at Google Scholar · View at Scopus
  15. O. Koul, H. Kaur, S. Goomber, and S. Wahab, “Bioefficacy and mode of action of rocaglamide from Aglaia elaeagnoidea (syn. A. roxburghiana) against gram pod borer, Helicoverpa armigera (Hübner),” Journal of Applied Entomology, vol. 128, no. 3, pp. 177–181, 2004. View at Google Scholar · View at Scopus
  16. G. A. Kraus and J. O. Sy, “A synthetic approach to rocaglamide via reductive cyclization of δ-keto nitriles,” Journal of Organic Chemistry, vol. 54, no. 1, pp. 77–83, 1989. View at Google Scholar · View at Scopus
  17. A. E. Davey, M. J. Schaeffer, and R. J. K. Taylor, “Synthesis of the novel anti-leukaemic tetrahydrocyclopenta[b]benzofuran, rocaglamide,” Journal of the Chemical Society—Series, no. 16, pp. 1137–1139, 1991. View at Google Scholar · View at Scopus
  18. A. E. Davey, M. J. Schaeffer, and R. J. K. Taylor, “Synthesis of the novel anti-leukaemic tetrahydrocyclopenta[b]benzofuran, rocaglamide and related synthetic studies,” Journal of the Chemical Society, Perkin Transactions 1, no. 20, pp. 2657–2666, 1992. View at Google Scholar · View at Scopus
  19. T. Watanabe, S. Kohzuma, T. Takeuchia, M. Otsuka, and K. Umezawa, “Total synthesis of (±)-aglaiastatin, a novel bioactive alkaloid,” Chemical Communications, no. 10, pp. 1097–1098, 1998. View at Google Scholar · View at Scopus
  20. N. Diedrichs, J. P. Ragot, and K. Thede, “A highly efficient synthesis of rocaglaols by a novel α-arylation of ketones,” European Journal of Organic Chemistry, no. 9, pp. 1731–1735, 2005. View at Publisher · View at Google Scholar · View at Scopus
  21. A. E. Davey and R. J. K. Taylor, “A novel 1,3-dithiane-based cyclopenta-annellation procedure: synthesis of the rocaglamide skeleton,” Journal of the Chemical Society, Chemical Communications, no. 1, pp. 25–27, 1987. View at Publisher · View at Google Scholar · View at Scopus
  22. M. R. Dobler, I. Bruce, F. Cederbaum et al., “Total synthesis of (±)-rocaglamide and some aryl analogues,” Tetrahedron Letters, vol. 42, no. 47, pp. 8281–8284, 2001. View at Publisher · View at Google Scholar · View at Scopus
  23. H. Li, B. Fu, M. A. Wang et al., “Total synthesis and biological activity of (±)-rocaglamide and its 2,3-di-epi analogue,” European Journal of Organic Chemistry, no. 10, pp. 1753–1758, 2008. View at Publisher · View at Google Scholar · View at Scopus
  24. J. A. Malona, K. Cariou, and A. J. Frontier, “Nazarov cyclization initiated by peracid oxidation: the total synthesis of (±)-rocaglamide,” Journal of the American Chemical Society, vol. 131, no. 22, pp. 7560–7561, 2009. View at Publisher · View at Google Scholar · View at Scopus
  25. S. R. Landor and P. D. Landor, The Chemistry of Allenes, Academic Press, New York, NY, USA, 1982.
  26. B. M. Trost, P. D. Greenspan, B. V. Yang, and M. G. Saulnier, “An unusual oxidative cyclization. A synthesis and absolute stereochemical assignment of ()-rocoglamide,” Journal of the American Chemical Society, vol. 112, no. 24, pp. 9022–9024, 1990. View at Publisher · View at Google Scholar · View at Scopus
  27. B. Gerard, G. Jones, and J. A. Porco, “A biomimetic approach to the rocaglamides employing photogeneration of oxidopyryliums derived from 3-hydroxyflavones,” Journal of the American Chemical Society, vol. 126, no. 42, pp. 13620–13621, 2004. View at Publisher · View at Google Scholar · View at Scopus
  28. B. Gerard, S. Sangji, D. J. O'Leary, and J. A. Porco, “Enantioselective photocycloaddition mediated by chiral Brønsted acids: asymmetric synthesis of the rocaglamides,” Journal of the American Chemical Society, vol. 128, no. 24, pp. 7754–7755, 2006. View at Publisher · View at Google Scholar · View at Scopus
  29. I. Bruce, N. G. Cooke, L. J. Diorazio, R. G. Hall, and E. Irving, “Synthesis of the carbocyclic analogue of (±)-Rocaglamide,” Tetrahedron Letters, vol. 40, no. 22, pp. 4279–4282, 1999. View at Publisher · View at Google Scholar · View at Scopus
  30. M. W. Giese and W. H. Moser, “Stereoselective synthesis of the rocaglamide skeleton via a silyl vinylketene formation/[4 + 1] annulation sequence,” Organic Letters, vol. 10, no. 19, pp. 4215–4218, 2008. View at Publisher · View at Google Scholar · View at Scopus