Isoaurones: synthesis and stereochemical assignments of geometrical isomers

A series of isoaurones have been synthesized for the first time from substituted acetophenones via benzo-2(3H)-furanone in three steps. Geometrical isomers of the isoaurones were separated. The differences in the proton and carbon NMR spectra of the E- and Z-isoaurones afford a useful method for distinguishing between the two isomers. Marginalin, a metabolite of Dytiscus marginalis has been synthesized and the spectral data of the synthetic E-isomer were in good agreement with those of the natural product. The antioxidant activity of isoaurones was determined by superoxide free radical (NBT) method and isoaurones 12 and 13 displayed excellent antioxidant activity.