Lipase-mediated flow synthesis of nature-inspired phenolic carbonates.

A facile and convenient lipase-catalyzed flow approach for the chemoselective synthesis of tyrosol and hydroxytyrosol methyl carbonates has been developed in neat dimethylcarbonate. The products were obtained in quantitative yield with high catalyst productivity. The biocatalytic approach was then exploited for the preparation of value-added symmetrical tyrosol and hydroxytyrosol carbonates.

Flow Synthesis of Nature-Inspired Mitochondria-Targeted Phenolic Derivatives as Potential Neuroprotective Agents.

A series of phenolic derivatives designed to selectively target mitochondria were synthesized under flow conditions starting from natural phenolic acids. The two-step continuous flow protocol, performed in Cyrene, a bioavailable dipolar aprotic solvent, allowed the isolation of the MITO compounds in moderate to good yields. The MITO compounds obtained, as a first step, were tested for their safety by cell viability analysis. The cytocompatible dose, in human neuronal cell line SH-SH5Y, depends on the type of compound and the non-toxic dose is between 3.5 and 125 µM. Among the seven MITO compounds synthesized, two of them have shown interesting performances, being able to protect mitochondria from oxidative insult.