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Concise Synthesis of (±)-Perrottetinene with Bibenzyl Cannabinoid

  • Park, Byung-Ho (School of Chemical Engineering and Technology, Yeungnam University) ;
  • Lee, Yong-Rok (School of Chemical Engineering and Technology, Yeungnam University)
  • Received : 2010.06.29
  • Accepted : 2010.07.28
  • Published : 2010.09.20
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Abstract

Keywords

References

  1. Gaoni, Y.; Mechoulam, R. J. Am. Chem. Soc. 1964, 86, 1646. https://doi.org/10.1021/ja01062a046
  2. Porter, A. C.; Felder, C. C. Pharmacol. Ther. 2001, 90, 45. https://doi.org/10.1016/S0163-7258(01)00130-9
  3. Williamson, E. M.; Evans, F. J. Drugs 2000, 60, 1303. https://doi.org/10.2165/00003495-200060060-00005
  4. Hollister, L. E. Pharmacol. Rev. 1986, 38, 1.
  5. Razdan, R. K. In The Total Synthesis of Natural Products; ApSimon, J., Ed.; Wiley: New York, 1981; Vol. 4, p 185.
  6. Consroe, P.; Fish, B. S. Med. Hypotheses 1981, 7, 1079. https://doi.org/10.1016/0306-9877(81)90103-1
  7. Consroe, P.; Fish, B. S. Commun. Psychopharmacol. 1980, 4, 287.
  8. Fish, B. S.; Consroe, P. Experientia 1981, 37, 295. https://doi.org/10.1007/BF01991664
  9. Razdan, R. K. Pharmacol. Rev. 1986, 38, 75.
  10. Ben-Zvi, Z.; Mechoulam, R.; Edery, H.; Porath, G. Science 1971, 174, 951. https://doi.org/10.1126/science.174.4012.951
  11. Mechoulam, R.; Varconi, H.; Ben-Zvi, Z.; Edery, H.; Grunfeld, Y. J. Am. Chem. Soc. 1972, 94, 7930. https://doi.org/10.1021/ja00777a049
  12. Martin, P.; Consroe, P. Science 1976, 194, 965. https://doi.org/10.1126/science.982057
  13. Matsuda, L. A.; Lolait, S. J.; Brownstein, M. J.; Young, A. C.; Bonner, T. I. Nature 1990, 346, 561. https://doi.org/10.1038/346561a0
  14. Munro, S.; Thomas, K. L.; Abu-Shaar, M. Nature 1993, 365, 61. https://doi.org/10.1038/365061a0
  15. Edery, H.; Grunfeld, Y.; Nen-Zvi, Z.; Mechoulam, R. Ann. N.Y. Acad. Sci. 1971, 191, 40. https://doi.org/10.1111/j.1749-6632.1971.tb13985.x
  16. Mendizabal, V. E.; Adler-Graschinsky, E. British J. Pharmacol. 2007, 151, 427. https://doi.org/10.1038/sj.bjp.0707261
  17. Ashton, C. H.; Moore, P. B.; Gallagher, P.; Young, A. H. J. Psychopharmaol. 2005, 19, 293. https://doi.org/10.1177/0269881105051541
  18. Toyata, M.; Shimamura, T.; Ishii, H.; Renner, M.; Braggins, J.; Asakawa, Y. Chem. Pharm. Bull. 2002, 50, 1390. https://doi.org/10.1248/cpb.50.1390
  19. Song, Y.; Hwang, S.; Gong, P.; Kim, D.; Kim, S. Org. Lett. 2008, 10, 269. https://doi.org/10.1021/ol702692q
  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.; Lee, W. K.; Noh, S. K.; Lyoo, W. S. Synthesis 2006, 853.
  22. Lee, Y. R.; Kim, D. H. Synthesis 2006, 603.
  23. Lee, Y. R.; Kim, J. H. Synlett 2007, 2232.
  24. Wang, X.; Lee, Y. R. Tetrahedron Lett. 2007, 48, 6275. https://doi.org/10.1016/j.tetlet.2007.07.022
  25. Wang, X.; Lee, Y. R. Synthesis 2007, 3044.
  26. Lee, Y. R.; Xia, L. Synthesis 2007, 3240.
  27. Lee, Y. R.; Kim, Y. M. Helv. Chim. Acta 2007, 90, 2401. https://doi.org/10.1002/hlca.200790247
  28. Lee, Y. R.; Li, X.; Kim, J. H. J. Org. Chem. 2008, 73, 4313. https://doi.org/10.1021/jo800367r
  29. Xia, L.; Lee, Y. R. Synlett 2008, 1643.
  30. Lee, Y. R.; Hung, T. V. Tetrahedron 2008, 64, 7338. https://doi.org/10.1016/j.tet.2008.05.053
  31. Lee, Y. R.; Wang, X. Tetrahedron 2009, 65, 10125. https://doi.org/10.1016/j.tet.2009.10.045
  32. Lee, Y. R.; Kim, Y. M.; Kim, S. H. Tetrahedron 2009, 65, 101. https://doi.org/10.1016/j.tet.2008.10.101
  33. Jung, D. H.; Lee, Y. R.; Kim, S. H. Helv. Chim. Acta 2010, 93, 635. https://doi.org/10.1002/hlca.200900251
  34. Lee, Y. R.; Xia, L. Tetrahedron Lett. 2008, 49, 3283. https://doi.org/10.1016/j.tetlet.2008.03.075
  35. Snider, B. B.; Lobera, M. Tetrahedron Lett. 2004, 45, 5015. https://doi.org/10.1016/j.tetlet.2004.05.005

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