One-pot chemoenzymatic access to a cefuroxime precursor via C1 extension of furfural†

Abstract

In this work, one-pot three-step synthesis of (Z)-2-methoxyimino-2-(furan-2-yl)acetic acid (SMIA), a key precursor for cefuroxime, was reported from biomass-derived furfural in 81% yield via sequential whole-cell catalytic hydroxymethylation by Escherichia coli harboring pyruvate decarboxylase, chemoenzymatic oxidation by the laccase-TEMPO system, and spontaneous oximation. In gram-scale production, SMIA was obtained in 63% isolated yield.