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Synthesis 1993; 1993(11): 1155-1158
DOI: 10.1055/s-1993-26019
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Enzyme-Mediated Regioprotection-Deprotection of Hydroxyl Groups in (+)-Catechin

Daniela Lambusta* , Giovanni Nicolosi, Angela Patti, Mario Piattelli
  • *Instituto del CNR per lo Studio delle Sostanze Naturali di Interesse Alimentare e Chimico-Farmaceutico, Via del Santuario 110, I-95028 Valverde CT, Italy
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Publication Date:
29 April 2002 (online)

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Several mono- and polyacetates of (+)-catechin [(2R,3S)-2-(3, 4-di-hydroxyphenyl)-3,4-dihydro-2H-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.