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A Simple Synthesis of Nordihydroguaiaretic Acid and Its Analogues

  • Published : 2005.07.20

Abstract

Keywords

References

  1. Turner, R. M.; Bowers, J. E.; Burgess, T. L. Sonoran Desert Plants, An Encological Atlas; The University of Arizona Press: Tucson, 1995; pp 255-259
  2. Botkin, C. W.; Duisberg, P. C. N. Mex. Col. Agr. Mech. Arts. Agr. Expt. Sta. Bull. No. 349, 1949, 18 (CA 1949, 43, 9174)
  3. The Merck Index, 11th Ed.; Merck and Company: Rathway, New Jersey, 1989; p 6610
  4. First report on the isolation of NDGA: Waller, C. W.; Gisvold, O. J. Am. Pharm. Assoc., Sci. Ed. 1945, 34, 78-81. (CA 1945, 39, 2097)
  5. Lundberg, W. O.; Halvorson, H. O.; Burr, G. O. Oil & Soap 1944, 21, 33-35 (CA 1944, 38, 2228) https://doi.org/10.1007/BF02593156
  6. Higgins, J. W.; Black, H. C. Oil & Soap 1944, 21, 277 (CA 1944, 38, 6118) https://doi.org/10.1007/BF02565474
  7. Skaltsa, H.; Bermejo, P.; Lazari, D.; Silvan, A. M.; Skaltsounis, A.-L.; Sanz, A.; Abad, M. J. Biol. Pharm. Bull. 2000, 23, 47 https://doi.org/10.1248/bpb.23.47
  8. Steele, V. E.; Holmes, C. A.; Hawk, E. T.; Kopelovich, L.; Lubet, R. A.; Crowell, J. A.; Sigman, C. C.; Kelloff, G. J. Expert Opin. Investig. Drugs 2000, 9, 2121 https://doi.org/10.1517/13543784.9.9.2121
  9. Whitman, S.; Gezginci, M.; Timmermann, B. N.; Holman, T. R. J. Med. Chem. 2002, 45, 2659 https://doi.org/10.1021/jm0201262
  10. Chen, H.; Teng, L.; Li, J. N.; Park, R.; Mold, D. E.; Gnabre, J.; Tseng, W. N.; Huang, R. C. J. Med. Chem. 1998, 41, 3001 https://doi.org/10.1021/jm980182w
  11. Hwu, J. R.; Tseng, W. N.; Gnabre, J.; Giza, P.; Huang, R. C. J. Med. Chem. 1998, 41, 2994 https://doi.org/10.1021/jm970819w
  12. Craigo, J.; Callahan, M.; Huang, R. C.; DeLucia, A. L. Antivir. Res. 2000, 47, 19 https://doi.org/10.1016/S0166-3542(00)00089-9
  13. Reed, M. J.; Meszaros, K.; Entes, L. J.; Claypool, M. D.; Pinkett, J. G.; Brignetti, D.; Luo, J.; Khandwala, A.; Reaven, G. M. Diabetologia 1999, 42, 102 https://doi.org/10.1007/s001250051121
  14. Huang, R. C. C.; Heller, J. D.; Hwu, J. R.; King, K. Y. US patent 6417234 B1 20020709
  15. Heller, J. D.; Kuo, J.; Wu, T. C.; Kast, W. M.; Huang, R. C. C. Cancer Res. 1994, 54, 1991s
  16. Heller, J. D.; Kuo, J.; Wu, T. C.; Kast, W. M.; Huang, R. C. C. Cancer Res. 2001, 61, 5499
  17. Li, G.; Ju, H. K.; Chang, H. W.; Jahng, Y.; Lee, S.-H.; Son, J.-K. Biol. Pharm. Bull. 2003, 26, 1039 https://doi.org/10.1248/bpb.26.1039
  18. Schroter, G.; Lichtenstadt, L.; Irineu, D. Ber. 1918, 51, 1587 https://doi.org/10.1002/cber.19180510247
  19. Haworth, R. D.; Mavin, C. R.; Sheldrick, G. J. Chem. Soc. 1934, 1423 https://doi.org/10.1039/jr9340001423
  20. Haworth, R. D.; Richardson, T. J. Chem. Soc. 1935, 120 https://doi.org/10.1039/jr9350000120
  21. Perry, C. W.; Kalnins, M. V.; Deitcher, K. H. J. Org. Chem. 1972, 37, 4371 https://doi.org/10.1021/jo00799a605
  22. Liebermann, S. V.; Mueller, G. P.; Stiller, E. T. J. Am. Chem. Soc. 1947, 69, 1540
  23. Sakakibara, Y. Nippon Kagaku Zasshi 1952, 73, 235 https://doi.org/10.1246/nikkashi1948.73.235
  24. Blears, J. G.; Haworth, R. D. J. Chem. Soc., Abstracts 1958, 1985
  25. Hearon, W. M.; MacGregor, W. S. Chem. Rev. 1955, 55, 957 https://doi.org/10.1021/cr50005a003
  26. Gezginci, M. H.; Timmermann, B. N. Tetrahderon Letters 2001, 42, 6083 https://doi.org/10.1016/S0040-4039(01)01182-0
  27. Gu, W. X.; Wu, A. X.; Gao, Q.; Pan, X. F. Chin. Chem. Letters 2000, 11, 15
  28. Xia, Y. M.; Cao, X. P.; Peng, K.; Ren, X. F.; Pan, X. F. Chin. Chem. Letters 2003, 14, 359
  29. Minato, A.; Tamao, K.; Susuki, K.; Kumada, M. Tetrahderon Letters 1980, 21, 4017 https://doi.org/10.1016/S0040-4039(00)92859-4
  30. Takeya, T.; Ohguchi, A.; Ara, Y.; Tobinaga, S. Chem. Pharm. Bull. 1994, 42, 430 https://doi.org/10.1248/cpb.42.430
  31. Biniecki, S.; Krajewski, E. Acta Pol. Pharm. 1960, 17, 421. (CA 1961, 55, 75898)
  32. Fujisawa, T.; Deguchi, Y. Yakugaku Zasshi 1954, 74, 975
  33. Zappala, M.; Grasso, S.; MIcale, N.; Polimeni, S.; De Michele, C. Synth. Comm. 2002, 32, 527 https://doi.org/10.1081/SCC-120002397
  34. Clemo, G. R.; Turnbull, J. H. J. Chem. Soc., Abstracts 1945, 533
  35. Murphy, S. T.; Ritchie, E.; Taylor, W. C. Aust. J. Chem. 1975, 28, 81 https://doi.org/10.1071/CH9750081
  36. Shimomura, H.; Sashida, Y.; Oohara, M. Phytochemistry 1987, 26, 1513 https://doi.org/10.1016/S0031-9422(00)81847-6
  37. Schrecker, A. W. J. Am. Chem. Soc. 1957, 79, 3823 https://doi.org/10.1021/ja01571a054
  38. Biftu, T.; Hazra, B. G.; Stevenson, R.; Williams, J. R. J. Chem. Soc., Perkin Trans. I 1978, 1978

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