Synthesis and Antibacterial Activity of α-Methylene-γ(β)-carboxy-γ-butyrolactones

Abstract

α-Methylene-γ(β)-carboxy-γ-butyrolactones (5 and 10) are considered to have strong antibacterial activity owing to large absolute electronegativity (χ), electron transfer(ΔΝ) and stabilization energy(ΔΕ) compared to potent cyclopentanone antibiotics. α-Methylene-γ-carboxy-γ-butyrolactone(5) was synthesized starting from L-glutamic acid and α-methylene-β-carboxy-γ-butyrolactone (α-methylene paraconic acid 10) was obtained via ethyl α-formylsuccinate(6) or hydroxymethylation of ethyl α-carbethoxysuccinate(11). α-Methylenationed 5 and 10 showed no strong antibacterial activity as we expected formerly.