Enantioselective hydrolysis of dihydrobenzofuranone and dihydroindolone derivatives with chemoenzymatic reactions

Benzofuranone and indole compounds are presenses extensively in natural products which are very important in asymmetric synthesis, since these type of derivatives contain stereocenter in their structures. In addition Benzofuranone and indole derivatives exposes important biological activities such as antiulcer, antioxidant, antidepressant, antibacterial, antifungal, antibiotic, anticancer, anti-HIV-1, antileichmanial and anti-angiogenesis agent. In this study, robust synthetised drug precursor compounds aimed to obtain in high enantiomerical purity, yield and selectivity with biotechnologic and chemical methods by using lipase enzymes. For this purpose, firstly we synthetised 6,7-dihydro-6-methylbenzofuran-4(5H)-one derivate, then acylated into 4,5,6,7-tetrahydro-6-methyl-4-oxobenzofuran-5-yl acetate and 4,5,6,7-tetrahydro-6-methyl-4-oxobenzofuran-7-yl acetate by using manganese (III) acetate-mediated acetoxylation, and followed by the lipase enzyme-mediated kinetic resolution of acetoxy benzofuranone derivatives in good yields and high enantiomeric excesses.