Enzyme-Mediated Regioprotection-Deprotection of Hydroxyl Groups in (+)-Catechin

All articles of this category Several mono- and polyacetates of (+)-catechin [(2 R ,3 S )-2-(3, 4-di-hydroxyphenyl)-3,4-dihydro-2 H -1-benzopyran-3,5,7-triol] have been synthesized by biocatalyzed reactions starting from (+)-catechin or (+)-catechin pentaacetate. In particular, 5- O -acetylcatechin and 7- O -acetylcatechin have been obtained by reaction of catechin with vinyl acetate in the presence of supported Pseudomonas cepacia lipase, while alcoholysis of catechin pentaacetate with 1-butanol catalyzed by the same enzyme yielded 3,3′,4′,5- O -tetraacetylcatechin and 3,3′,4′- O -triacetylcatechin and, under different experimental conditions, 3- O -acetylcatechin.