Easy synthesis of polyphenolic 4-thiaflavans with a ‘double-faced’ antioxidant activity

Inverse electron demanding Diels–Alder reactions of o-thioquinones with styrenes, followed by simple manipulations of the obtained cycloadducts, allowed the synthesis of polyphenolic 4-thiaflavans which showed antioxidant activity miming either flavonoid or tocopherol behaviour.