Preparation of Key Intermediates for the Syntheses of Coenzyme Q10 and Derivatives by Cross-Metathesis Reactions

Abstract

An alternative catalytic strategy for the preparation of benzylmethacrylate esters, key intermediates in the synthesis of coenzyme Q10 and derivatives, was reported. This strategy avoided undesirable stoichiometric reduction/oxidation processes by utilizing the catalytic formation of allylarenes and then cross-metathesis to selectively form E-benzylmethacrylate esters with good yields (58–64%) and complete E-selectivity. The ester intermediates were reduced to common key benzylallylic alcohols (90–92% yield), which were subsequently used in the formal syntheses of coenzyme Q10 and one derivative.