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The effect of oxidation degree at the benzylic position of 2,3-dibenzyl-4-butanolide and 3,4-dibenzyltetrahydrofuran lignans on the antimicrobiological activity was examined. The highest oxidation degree at the benzylic position of 2,3-dibenzyl-4-butanolide gave the greatest activity, and 3,4-dibenzoyltetrahydrofuran showed the highest antifungal activity. The relationship between stereochemistry and activity was also examined. Both enantiomers of cis-matairesinol were synthesized for the first time, one of the cis-matairesinols showing antibacterial activity.

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