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A Model Study Directed Towards a Practical Enantioselective Total Synthesis of (-)-Morphine
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1992
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Combinatorial ChemistryStereogenic CentersBioorganic ChemistryEngineeringOrganic ChemistryChemistryHeterocycle ChemistryMedicinal ChemistryStereoselective SynthesisCatalysisPharmacologyNatural Product SynthesisAsymmetric CatalysisEnantioselective SynthesisHeterocyclicNatural SciencesKey CompoundsCope RearrangementSynthetic ChemistryDrug Discovery
A tricyclic ring system 10 containing the stereogenic centers of the nonaromatic portion of morphine (1) has been prepared in eight steps from toluene by the combination of microbial oxidation and intramolecular Diels-Alder cycloaddition followed by a Cope rearrangement. Experimental and spectral data are provided for all key compounds and potential for a short synthesis of morphine is indicated.