Synthesis of (-)-morphine.

@article{Taber2002SynthesisO,
  title={Synthesis of (-)-morphine.},
  author={D. Taber and T. D. Neubert and A. Rheingold},
  journal={Journal of the American Chemical Society},
  year={2002},
  volume={124 42},
  pages={
          12416-7
        }
}
  • D. Taber, T. D. Neubert, A. Rheingold
  • Published 2002
  • Chemistry, Medicine
  • Journal of the American Chemical Society
    • The preparation of the diastereomerically pure beta-tetralone ketal 4 is reported. Intramolecular alkylidene C-H insertion followed by hydrolysis of 4 proceeded to give the enantiomerically pure cyclopentene 15. The key step in this synthesis was the bis-intramolecular cyclization of keto aldehyde 2 to give the tetracyclic intermediate 20. Enone 20 was converted over several steps to (-)-morphine 1. 
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    References

    SHOWING 1-10 OF 17 REFERENCES
    Sodium Bis(2-methoxyethoxy)aluminum Hydride
    • 3
    For leading references to previous syntheses of enantiomerically
    • 2001
    J. Org. Chem
    • J. Org. Chem
    • 1995
    Attempted epoxidation with peracids led to extensive decomposition
    • 1988
    Recl
    • 1979
    (6) For leading references to previous approaches to the ring system of morphine
    • (6) For leading references to previous approaches to the ring system of morphine
    • 1973
    Reductive cleavage of sulfonamides with sodium bis(2-methoxyethoxy)aluminum hydride
    • 59
    Br. J. Anaesth. AdV. Neuroimmunol. Eur. J. Pharmacol
    • Br. J. Anaesth. AdV. Neuroimmunol. Eur. J. Pharmacol
    • 1967
    Chem. Soc. J. Med. Chem. J. Med. Chem. J. Am. Chem. Soc
    • Chem. Soc. J. Med. Chem. J. Med. Chem. J. Am. Chem. Soc
    • 1900
    (5) For leading references to previous syntheses of racemic morphine
    • (5) For leading references to previous syntheses of racemic morphine
    • 1109