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Synthesis of Lophirone C using coconut peroxidase

Lophirone C is a lignan with several pharmacological activities reported such as anticarcinogenicity and antioxidation activities. The bark of Lophira spp contains that lignan. Due to those important properties, the purpose of this work is the organic and enzymatic synthesis of Lophirone C. Starting from the methylation of resorcinol with methyl iodide using potassium carbonate as base, the product was acylated by a mixture of acetic anhydride and trifluoroacetic acid, so providing the acetophene. Following step was the aldol condensation of this ketone with 4-methoxybenzaldehyde, using ethanol as solvent and potassium tert-butoxide as base. With the chalcone formed, the deprotection of the phenolic hydroxyls and subsequent oxidative coupling provides the final product with synthetic Lophirone C.

Keywords: aldol reaction, Lophirone c, lignan, chalcone dimers, stem bark, coconut peroxidase, organic synthesis