Levoglucosenone (LGO), a valuable chiral platform chemical that can be efficiently produced from catalytic fast pyrolysis of cellulose, has been efficiently converted into optically pure (S)-γ-hydroxymethyl-α,β-butenolide (HBO) using a two-step sequence involving a lipase-mediated Baeyer–Villiger oxidation and an acid hydrolysis. In the same fashion, (S)-γ-hydroxymethyl-γ-butyrolactone (2H-HBO) was successfully obtained through a three-step sequence (Baeyer–Villiger, palladium-catalysed hydrogenation and acid hydrolysis). The use of solid buffers in the lipase-mediated Baeyer–Villiger oxidation has proved beneficial in two ways: not only the reaction time and the enzymatic load were both reduced four-fold (from 8 to 2 hours and 464 to 113 U mmol⁻¹) to reach conversions ≥83%, but solid buffers also prevented lipase from denaturation, thus preserving its enzymatic activity and allowing its use for further oxidation cycles.

Aqueous H ₂ O ₂ -mediated Baeyer–Villiger oxidation of levoglucosenone provides valuable chiral lactone HBO in one step without an organic solvent, catalyst nor acid.

Naturally occurring sinapic acid and its esters are anti-UV and antiradical chemicals. This work aimed at designing an industrially relevant sustainable synthetic pathway allowing their selective β–β′ dimerization to enhance their properties with a view to use them in commercial applications such as functional additives for cosmetics, plastics and food/feed. A copper(I)-catalyzed procedure involving pyridine and O₂ from air was developed and greened up using the REACH-compliant bio-based solvent Cyrene™. Upon optimizing further through design of experiments, this sustainable synthetic process was successfully implemented to various sinapate esters and was validated on the multigram scale. Antiradical activities of the resulting β–β′ disinapate esters were benchmarked against commercial antioxidants, whereas their UV absorbance was compared to that of sinapoyl malate, a natural anti-UV compound found in plants and that of Octinoxate™, a widely used commercial sunscreen ingredient. Results showed that these dimers were better radical scavengers, and not only exhibited a better UV absorbance but also covered both UV-A and UV-B regions.