The studies on chemoenzymatic synthesis of Femoxetine

The studies on enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid esters were performed. The obtained results demonstrated that the careful choice of biocatalyst and a reaction type are very important for successful enzymatic kinetic resolution. Kinetic resolution provides 3-phenyl-4-pentenoic acid (1) with good enantioselectivity upon esterification. That product was used as a substrate for formal synthesis of two biologically relevant compounds Femoxetine and LG 121071.

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► We determined the conditions for enzymatic kinetic resolution of 3-phenyl-4-pentenoic acid esters.
► Two different reaction protocols for kinetic resolution of target compound were performed providing 3-phenyl-4-pentenoic acid esters in very good enantioselectivity.
► The influence of enzymes on kinetic resolution was determined.
► Six step formal total synthesis of Femoxetine based on chiral 3-phenyl-4-pentenoic acid was performed.