Development of pharmaceutically relevant bio-based intermediates though aldol condensation and Claisen–Schmidt reactions of dihydrolevoglucosenone (Cyrene®)

Abstract

Dihydrolevoglucosenone (Cyrene®) has been successfully utilised as a bio-based platform molecule for the synthesis of pharmaceutically relevant intermediates through aldol condensation reactions. Utilising sustainable synthetic methodologies, the self-aldol condensation reaction of Cyrene was achieved in high purity, with isolated yields of 81.3%. Claisen–Schmidt reactions with a range of aromatic and heteroaromatic aldehydes yielded several previously unreported Cyrene-based compounds, characterised by single-crystal X-ray diffraction, FT-IR, NMR and MS.