Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
권호 표지
DOI QR코드

DOI QR Code

Novel Synthesis of the Natural Protoberberine Alkaloids: Oxypalmatine and Oxypseudopalmatine

  • Le, Thanh Nguyen (College of Pharmacy and Research Institute of Drug Development, Chonnam National University) ;
  • Cho, Won-Jea (College of Pharmacy and Research Institute of Drug Development, Chonnam National University)
  • Published : 2007.05.20
Download PDF
⟨ Previous Next ⟩

Abstract

Oxypalmatine and oxypseudopalmatine were synthesized in three steps from the benzonitrile 11 and toluamides 12a, b. The lithiated cycloaddition reaction yielded 3-arylisoquinolinone intermediates. A subsequent internal SN2 reaction produced the corresponding 8-oxoprotoberberines, oxypalmatine and oxypseudopalmatine.

Keywords

References

  1. Bhakuni, D. S.; Jain, S. Protoberberine Alkaloids in The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 28
  2. Shamma, M. The Isoquinoline Alkaloids. Chemistry and Pharmacology; Blomquist, A. T., Wasserman, H., Eds.; Academic Press: New York, 1972; Vol. 25, p 268
  3. Southon, I. W.; Buckingham, J. Dictionary of Alkaloids; Chapman and Hall: London, 1989
  4. Bentley, K. W. The Isoquinoline Alkaloids; Ravindranath, B., Ed.; Harwood Academic: Bangalore, 1998; Vol. 1, p 219
  5. Chang, F.-R.; Wu, Y.-C. J. Nat. Prod. 2005, 68, 1056 https://doi.org/10.1021/np050082a
  6. Faizi, S.; Khan, R. A.; Azher, S.; Khan, S. A.; Tauseef, S.; Ahmad, A. Planta Medica 2003, 69, 350 https://doi.org/10.1055/s-2003-38883
  7. Zhang, J.-S.; Men-Olivier, L.; Massiot, G. Phytochemistry 1995, 39, 439
  8. Pinho, P. M. M.; Pinto, M. M. M.; Kijjoa, A.; Pharadai, K.; Diaz, J. G.; Herz, W. Phytochemistry 1992, 31, 1403 https://doi.org/10.1016/0031-9422(92)80301-T
  9. Patra, A.; Montgomery, C. T.; Freyer, A. J.; Guinaudeau, H.; Shamma, M.; Tantisewie, B.; Pharadai, K. Phytochemistry 1987, 26, 547 https://doi.org/10.1016/S0031-9422(00)81451-X
  10. Weimar, C.; Von Angerer, S.; Wiegrebe, W. Arch. Pharm. 1991, 324, 509 https://doi.org/10.1002/ardp.2503240810
  11. Ninomiya, I.; Naito, T.; Takasugi, H. J. Chem. Soc. Perkin I 1975, 1720
  12. Kametani, T.; Sugai, T.; Shoji, Y.; Honda, T.; Satoh, F.; Fukumoto, K. J. Chem. Soc. Perkin I 1977, 1151
  13. Leung, W. C.; Zheng, H.; Huen, M.; Law, S. L.; Xue, H. Prog. Neuro. Psycho. Biol. Psych. 2003, 27, 775 https://doi.org/10.1016/S0278-5846(03)00108-8
  14. Chang, C.-K.; Lin, M.-T. Neuroscience Lett. 2001, 307, 163
  15. Liang, J.; Wang, F.; Zheng, P.; Liang, J. Zhongguo Yaolixue Tongbao 1999, 15, 167
  16. Le, T. N.; Gang, S.-K.; Cho, W.-J. J. Org. Chem. 2004, 69, 2768 https://doi.org/10.1021/jo035836+
  17. Le, T. N.; Cho, W.-J. Chem. Pharm. Bull. 2006, 54, 476 https://doi.org/10.1248/cpb.54.476
  18. Le, T. N.; Cho, W.-J. Bull. Korean Chem. Soc. 2006, 27, 2093 https://doi.org/10.5012/bkcs.2006.27.12.2093
  19. Charlton, J. L.; Alauddin, M. M. J. Org. Chem. 1986, 51, 3490 https://doi.org/10.1021/jo00368a018
  20. Poindexter, G. S. J. Org. Chem. 1982, 47, 3787 https://doi.org/10.1021/jo00140a047
  21. Beugelmans, R.; Bois-Choussy, M. Tetrahedron 1992, 48, 8285
  22. Grigg, R.; Sridharan, V.; Stevenson, P.; Sukirthalingam, S.; Worakun, T. Tetrahedron 1990, 46, 4003 https://doi.org/10.1016/S0040-4020(01)90535-6
  23. Suau, R.; Lopez-Romero, J. M.; Ruiz, A.; Rico, R. Tetrahedron 2000, 56, 993
  24. Cobas, A.; Guitian, E.; Castedo, L. J. Org. Chem. 1992, 57, 6765 https://doi.org/10.1021/jo00051a018

Cited by

  1. A Convenient Synthesis of 2,3-Dihydro-3-methylidene-1H-isoindol-1-ones by Reaction of 2-Formylbenzo­nitriles with Dimethyloxosulfonium Methylide vol.93, pp.6, 2010, https://doi.org/10.1002/hlca.201000035
  2. Novel Synthesis of the Natural Protoberberine Alkaloids: Oxypalmatine and Oxypseudopalmatine. vol.38, pp.38, 2007, https://doi.org/10.1002/chin.200738197
  3. Total synthesis of 8-oxypseudopalmatine and 8-oxypseudoberberine via ring-closing metathesis vol.65, pp.49, 2009, https://doi.org/10.1016/j.tet.2009.10.027
  4. Synthesis of 12-oxobenzo[c]phenanthridinones and 4-substituted 3-arylisoquinolones via Vilsmeier-Haack reaction vol.68, pp.1, 2007, https://doi.org/10.1016/j.tet.2011.10.053
  5. Reaction Outcome Critically Dependent on the Method of Workup: An Example from the Synthesis of 1-Isoquinolones vol.86, pp.12, 2007, https://doi.org/10.1021/acs.joc.1c00561