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The presence of a methyl group in the vinylic moiety of substrates <jats:bold>3i<\/jats:bold>,<jats:bold>j<\/jats:bold> allowed the formation of two \u03b3,\u03b4\u2010monoepoxide diastereomers. The epoxidation of (<jats:italic>E<\/jats:italic>,<jats:italic>E<\/jats:italic>)\u20102\u2032\u2010hydroxycinnamylideneacetophenones <jats:bold>3h<\/jats:bold>,<jats:bold>j<\/jats:bold> led to the formation of the corresponding \u03b3,\u03b4\u2010monoepoxides as well as (<jats:italic>E<\/jats:italic>)\u20102,3\u2010<jats:italic>trans<\/jats:italic>\u20103\u2010hydroxy\u20102\u2010styryl\u20104\u2010chromanones, which originated from the in situ cyclisation of 2,3\u2010epoxy\u20101\u2010(2\u2010hydroxyphenyl)\u20105\u2010phenyl\u20104\u2010penten\u20101\u2010ones. The structures of all new compounds and the stereochemistry of the mono\u2010 and diepoxide diastereomers were established by NMR studies. (\u00a9 Wiley\u2010VCH Verlag GmbH &amp; Co. 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