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

Two trans-cyanostilbene derivatives were prepared, and their oxidative dimerizations promoted by horseradish peroxidase-H2O2 were investigated. An M5–M5-coupled biphenyl-type dimer was first synthesized from the biomimetic oxidative coupling reaction of 8-cyano-resveratrol. A novel M5–MO-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. [ABSTRACT FROM AUTHOR]