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An Efficient Synthesis of a Key Intermediate of DU-6859a via Asymmetric Microbial Reduction.
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1998
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Artificial IntelligenceCombinatorial ChemistryMedicinal ChemistryBioorganic ChemistryKey IntermediateEngineeringAsymmetric Microbial ReductionNatural SciencesEfficient Synthesis MethodSynthetic BiologyOrganic ChemistrySynthesis Design SystemMicrobiologyEfficient SynthesisNatural Product SynthesisSynthetic ChemistryEnantioselective SynthesisBiomolecular Engineering
An efficient synthesis method for the C-7 substituent of DU-6859a (1), which is a new-generation antibacterial quinolone carboxylic acid, was established by utilizing an enantioselective microbial reduction of 5-benzyl-4, 7-dioxo-5-azaspiro[2.4]heptane (7) to the corresponding chiral alcohol (8) as the key reaction. This synthetic method was based on use of AIPHOS (Artificial Intelligence for Planning and Handling Organic Synthesis), which is a synthesis design system that generates suitable retrosynthetic routes from the standpoints of both novelty and practicality.