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Two  trans -cyanostilbene derivatives were prepared, and their oxidative dimerizations promoted by horseradish peroxidase-H 2 O 2  were investigated. An M 5 –M 5 -coupled biphenyl-type dimer was first synthesized from the biomimetic oxidative coupling reaction of 8-cyano-resveratrol. A novel M 5 –M O-4 -coupled diarylether-type dimer was obtained through the oxidation of 3,5-dibromo-8-cyano-resveratrol and the following debromination reaction. The cyano group at the C-8 of two cyano-stilbenes had obvious influences on the regioselectivity of their coupling reactions.

Synthesis of biphenyl-type and diarylether-type oligostilbenes from the biomimetic oxidation of cyano-resveratrol derivatives