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Convenient Synthesis of Enantiopure β-Adrenergic Blockers: (R)-Nifenalol, (R)-Denopamine, (R)-Dichloroisoproterenol and (R)-Pronethalol


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References

  1. Crossley, R. Chirality and the Biological Activity of Drugs; CRC Press: New York, NY, 1995.
  2. Stinson, S. C. Chem. Eng. News 1992, 70(39), 46
  3. Stinson, S. C. Chem. Eng. News 1993, 71(39), 38
  4. Stinson, S. C. Chem. Eng. News 1995, 73(41), 44
  5. Stinson, S. C. Chem. Eng. News 1997, 75(42), 38
  6. Stinson, S. C. Chem. Eng. News 1999, 77(41), 101 https://doi.org/10.1021/cen-v077n041.p101
  7. Stinson, S. C. Chem. Eng. News 2000, 78(19), 59
  8. Stinson, S. C. Chem. Eng. News 2001, 79(40), 79.
  9. Office of Drug Evaluation and Research Guideline for Submitting Supporting Documentation in Drug Applications for the Manufacture of Drug Substances; FDA: Washington, D. C. Feb.1987.
  10. Waldeck, B. Chirality 1993, 5, 350. https://doi.org/10.1002/chir.530050514
  11. Ruffolo, R. R. Jr., Tetrahedron 1991, 47, 9953. https://doi.org/10.1016/S0040-4020(01)96045-4
  12. Kleemann, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances: Syntheses, Patents, Applications, 3rd ed; Verlag: New York, 1999.
  13. Murmann, W.; Rumore, G.; Gamba, A. Bull. Chim. Farm. 1967, 106, 609.
  14. Ikeo, T.; Nagao, T.; Suzuki, T.; Yabana, H.; Nakajima, H. Jpn. J. Pharmacol. 1985, 39, 191. https://doi.org/10.1254/jjp.39.191
  15. Ikezaki, M.; Umino, N.; Gaino, M.; Aoe, K.; Iwakuma, T.; Oh-ishi, T. Yakukaku Zasshi 1986, 106, 80.
  16. Almirante, L.; Murmann, W. J. Med. Chem. 1966, 9, 650. https://doi.org/10.1021/jm00323a002
  17. Howe R.; Rao, B. S. J. Med. Chem. 1968, 11, 1118. https://doi.org/10.1021/jm00312a003
  18. Solladie-Cavallo, A.; Diep-Vohuule, A. J. Org. Chem. 1995, 60, 3494. https://doi.org/10.1021/jo00116a041
  19. Pedragosa-Moreau, S.; Morisseau, C.; Baratti, J.; Zylber, J.; Archelas, A.; Furstoss, R. Tetrahedron 1997, 53, 9707. https://doi.org/10.1016/S0040-4020(97)00639-X
  20. Corey, E. J.; Link, J. O. J. Org. Chem. 1991, 56, 442. https://doi.org/10.1021/jo00001a084
  21. Brown, R. F. C.; Donohue, A. C.; Jackson, W. R.; McCarthy, T. D. Tetrahedron 1994, 50, 13739. https://doi.org/10.1016/S0040-4020(01)85686-6
  22. Gu, J.-X.; Li, Z.-Y.; Lin, G.-Q. Tetrahedron 1993, 49, 5805. https://doi.org/10.1016/S0040-4020(01)87947-3
  23. Howe, R.; Crowther, A. F.; Stephenson, J. S.; Rao, B. S.; Smith, L. H. J. Med. Chem. 1968, 11, 1000. https://doi.org/10.1021/jm00311a020
  24. Solladie-Cavallo, A.; Bencheqroun, M. J. Org. Chem. 1992, 57, 5831. https://doi.org/10.1021/jo00048a011
  25. Cho, B. T.; Yang, W. K.; Choi, O. K. J. Chem. Soc. Perkin Trans. 1 2001, 1204.

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