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Synthetic Studies of Carbapenem and Penem Antibiotics. V. Efficient Synthesis of the 1.BETA.-Methylcarbapenem Skeleton.
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1994
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V. Efficient SynthesisEngineeringOrganic ChemistryPharmaceutical ChemistryPractical One-pot PreparationMedicinal ChemistryDiversity Oriented SynthesisAntimicrobial Drug DiscoveryDieckmann-type CyclizationDiversity-oriented SynthesisDieckmann ReactionPharmacologyNatural Product SynthesisEnantioselective SynthesisBiomolecular EngineeringNatural SciencesSynthetic Chemistry1.Beta.-methylcarbapenem SkeletonPenem Antibiotics
An efficient synthesis of 1β-methylcarbapenem from the 1-(2-oxoazetidinyl)acetate 8 was developed by application of the Dieckmann reaction. Dieckmann-type cyclization of 8 and conversion to the enolphosphate 10 were achieved without epimerization to the 1α-methyl isomer in a one-pot procedure. Treatment with the mercaptan 22 after the phosphorylation resulted in a practical one-pot preparation of the 1β-methylcarbapenem derivative 23 from 8.