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A Stereoselective Synthesis of (R)-(-)-rolipram from L-Glutamic Acid
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1997
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Medicinal ChemistryEnantioselective SynthesisBiochemistryPure Michael ProductNatural SciencesMedicineL-glutamic AcidOrganic ChemistryStereoselective SynthesisPharmacologyPharmaceutical ChemistrySynthetic ChemistryBiomolecular EngineeringDrug DiscoveryNatural Product Synthesis
A stereoselective synthesis of (R)-(-)-rolipram from L-glutamic acid is described. The key step is a stereoselective Michael addition of an arylcuprate to a modified pyroglutamic derivative which acts as the template to induce the stereoselectivity. Facile manipulation of the enantiomerically pure Michael product afforded the expected therapeutic agent.