Synthesis of (-)-morphine.

@article{Taber2002SynthesisO,
  title={Synthesis of (-)-morphine.},
  author={Douglass F. Taber and Timothy D. Neubert and Arnold L Rheingold},
  journal={Journal of the American Chemical Society},
  year={2002},
  volume={124 42},
  pages={
          12416-7
        }
}
  • Douglass F. Taber, Timothy D. Neubert, Arnold L Rheingold
  • Published in
    Journal of the American…
     2002
  • Chemistry, Medicine
    • 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. 
    View on PubMed
    valhalla.chem.udel.edu
    24 Citations
    2 Highly Influenced Papers
    11 Cite Background
    1 Cite Methods

    Topics from this paper.

    Explore Further: Topics Discussed in This Paper

    Citations

    Publications citing this paper.
    SHOWING 1-10 OF 24 CITATIONS

    A Survey of Molecular Imaging of Opioid Receptors

    VIEW 6 EXCERPTS
    CITES BACKGROUND
    HIGHLY INFLUENCED

    Chemoenzymatic Total Synthesis of (+)-10-Keto-Oxycodone from Phenethyl Acetate †

    VIEW 3 EXCERPTS
    CITES BACKGROUND
    HIGHLY INFLUENCED

    Lewis acid catalyst system for Diels–Alder reaction

    DNA nanostructures for biotechnological applications

    Medications development for drug addiction and other neuropsychiatric disorders

    VIEW 1 EXCERPT
    CITES BACKGROUND

    Opioid and stimulant use among a sample of corrections-involved drug users : seeking an understanding of high-risk drug decisions within a system of constraint.

    The DARK Side of Total Synthesis: Strategies and Tactics in Psychoactive Drug Production.

    Molecular Characterization of the Opioid Receptors: Design, Development, and Preclinical Evaluation of Salvinorin A-Based Molecular Probes.

    VIEW 2 EXCERPTS
    CITES METHODS

    The Chemical History of Morphine: An 8000-year Journey, from Resin to de-novo Synthesis.

    VIEW 2 EXCERPTS
    CITES BACKGROUND

    Plant extracts and natural products : predictive structural and biodiversity-based analyses of uses, bioactivity, and 'research and development' potential

    References

    Publications referenced by this paper.
    SHOWING 1-9 OF 9 REFERENCES

    Sodium Bis(2-methoxyethoxy)aluminum Hydride

    For leading references to previous syntheses of enantiomerically

    • Przewlocka, J B.Eur.
    • 2001

    Attempted epoxidation with peracids led to extensive decomposition

    • C. Venturello, R. J. Org. D’Aloisio
    • 1988

    Recl

    • T. S. Lie, L. Maat, H. C. Beyerman
    • 1979

    Chem. 1972, 37, 2208. (b) Sodium bis(2-methoxyethoxy)aluminum hydride is sold as both Red-Al and Vitride

    • E H Gold, E J Babad, Org

    Chem. 1988, 53, 1553. (b) Attempted epoxidation with peracids led to extensive decomposition

    • C Venturello, R J Daposaloisio, Org

    Scheme 5 a a Conditions: (a) Red-Al, toluene, reflux; (b) ClCOOEt, Et3N

    The Z-bromoalkene alkylating agent was used to limit the complexity of 1 H NMR and 13 C NMR and also to simplify the chiral ketal product distribution and separation

    The first ketal diastereomer to elute via chromatography was converted to the p-bromobenzenesulfonamide i. This was determined by X-ray analysis to have the configuration at C-9, C-13, and C-14 shown

    • Tetralone 13 was initially ketalized with (R,R)-(+)-hydrobenzoin