Synthesis of acacetin and resveratrol 3,5-di-O-β-glucopyranoside using lipase-catalyzed regioselective deacetylation of polyphenol glycoside peracetates as the key step

• Lipase-catalyzed transesterification regioselectively proceeded at C-4′ acetate of a peracetylated form of rhoifolin.
• Acacetin was synthesized from naringin in 65% overall yield.
• Lipase-catalyzed transesterification regioselectively proceeded at C-4′ acetate of a peracetylated form of piceid.
• Resveratrol 3,5-diglucoside was synthesized from piceid in 62% overall yield.
• The blocking of the proper position with pre-installed sugar side chain was effective for the better regioselectivity.

Acacetin and resveratrol 3,5-di-O-β-glucopyranoside were synthesized from naturally abundant naringin and piceid in 65% and 62% overall yield, respectively. The key steps were the regioselective deacetylation of the peracetates of the glycosylated forms with Candida antarctica lipase B (Novozym 435) and Burkholderia cepacia lipase (Amano PS-IM). Deacetylation occurred exclusively at the least hindered position of the aromatic moieties and all acetyl groups in the sugar side chain remained intact. This excellent selectivity enabled regiospecific transformation of the liberated phenolic hydroxy groups, resulting in efficient synthesis of the target molecules.

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