The past seven years have witnessed significant progress in the biochemical characterization of dirigent (monolignol radical binding) proteins in vitro, as well as in the delineation of their associated metabolic networks in planta. Interestingly, both the stereoselective and regiospecific control over phenoxy radical-radical coupling appears to have evolved during the transition of plants to a land base for lignan, norlignan and ellagitannin biosynthesis.