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Studies on Antiviral Agents. III. Synthesis of Tenuazonic Acid Derivatives.
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1967
Year
Amino Acid EstersOrganic ChemistryAntiviral DrugL-amino AcidMedicinal ChemistryAntiviral Drug DevelopmentDerivativesDiversity-oriented SynthesisVirologyPharmacologyAntiviral CompoundNatural Product SynthesisEnantioselective SynthesisBiomolecular EngineeringTenuazonic Acid DerivativesNatural SciencesAntiviral TherapyMedicineDerivative (Chemistry)Synthetic ChemistryDrug Discovery
Tenuazonic acid derivatives were synthesized from amino acid esters by N-acetoacetylation with diketene followed by cyclization with sodium alkoxides. Some L-amino acid produced a small amount of DL-compounds in this process. N-Acetoacetyl group of diethyl aspartate cyclized to the α-ester group to form five-membered ring compound selectively. These compounds were condensed with carbonyl reagents.