Biocatalytic acylation studies on novel 3-aryl-3-hydroxymethyl-2, 3-dihydro-4H-1- benzopyran-4-ones

Abstract

(±)-3-Aryl-3-hydroxymethyl-2,3-dihydro-4H-1- benzopyran-4-ones have been synthesized in four steps starting with the coupling of resorcinol with corresponding phenylacetic acid leading to the formation of 2,4-dihydroxyphenyl aryl ketones, which upon monomethylation/benzylation and hydroxymethylation afford (±)-hydroxymethylisoflavanones in 65-70% yields. These isoflavanones have been subjected to lipase-catalyzed acylation reactions under different conditions (for optimization) of varying solvents, enzymes and acylating agents. Candida antarctica lipase B in tetrahydrofuran using heptanoic anhydride at 90 ºC is found to be the best reaction protocol for the biocatalytic reaction.