Synthesis of Coniferyl and Dihydroconiferyl Derivatives Using Radical Bromination with N-Bromosuccinimide as the Key Step.

Abstract

Coniferyl and dihydroconiferyl derivatives were synthesized by reacting bromides, obtained from allylic and benzylic brominations using N-bromosuccinimide (NBS), with appropriate nucleophiles. NBS bromination of eugenol acetate, followed by replacement of bromine by an acetoxy group and subsequent reduction with lithium aluminium hydride, afforded coniferyl alcohol in 65% overall yield. Due to the availability of the starting materials (eugenol and isoeugenol) and the good overall yields obtained, these synthetic routes compete well with other methods of preparation.