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

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 condensations 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 novel cyrene-based compounds, characterised by single-crystal X-ray diffraction, FT-IR, NMR and MS.