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In a recent study, we investigated the antimicrobial activity of a collection of resveratrol-derived monomers and dimers against a series of foodborne pathogens. Out of the tested molecules, dehydro-<i>&#948;</i>-viniferin and dehydro-<i>&#949;</i>-viniferin emerged as the most promising derivatives. To define the structural elements essential to the antimicrobial activity against the foodborne pathogen <i>L. monocytogenes</i> Scott A as a model Gram-positive microorganism, the synthesis of a series of simplified benzofuran-containing derivatives was carried out. The systematic removal of the aromatic moieties of the parent molecules allowed a deeper insight into the most relevant structural features affecting the activity. While the overall structure of compound <b>1</b> could not be altered without a substantial loss of antimicrobial activity, the structural simplification of compound <b>2</b> (minimal inhibitory concentration (MIC) 16 &#181;g/mL, minimal bactericidal concentration (MBC) &gt;512 &#181;g/mL) led to the analogue <b>7</b> with increased activity (MIC 8 &#181;g/mL, MBC 64 &#181;g/mL).