Synthesis of Dihydrobenzofuranone Derivatives with Biotechnological Methods

Year 2018, Volume: 5 Issue: 3, 1221 - 1232, 01.09.2018

Zerrin Zerenler Çalışkan , Ebru Nur Ay

https://doi.org/10.18596/jotcsa.448551

Cited By: 2

Abstract

Benzofuranone 
derivatives are important structural units in many biologically active
compounds thus, synthesis of these types of compounds in optically pure form
found increased interest in pharmaceutical chemistry. In this study, the
enantioselective synthesis of 4,5,6,7-tetrahydro-6-phenyl-4-oxo-benzofuranone-5-yl
acetate (3) and 4,5,6,7-tetrahydro-6-
phenyl-4-oxo-benzofuranone-5-yl hydroxy derivative (4) was carried out for the first time,  by enzyme-mediated hydrolysis reactions with
high enantiomeric excesses. Several lipases were used for the kinetic
resolution in different pH values and different solvent systems of racemic 4,5,6,7-tetrahydro-6-phenyl-4-oxo-benzofuranone-5-yl
acetate (rac-3) in which the lipases
from HPL, PPL,  RNL and PCL displayed
high enentioselectivity towards 4,5,6,7-tetrahydro-6- phenyl-4-oxo-benzofuranone-5-yl
hydroxy derivative (4)  at pH=7. 

Keywords

benzofuranone, enzyme-mediated hydrolysis, kinetic resolution

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