PARTIAL DEACETYLATION OF ASTERRIQUINONE DIACETATE BY AQUEOUS SODIUM BICARBONATE IN PYRIDINE

Abstract

Asterriquinone (ARQ); 2, 5-bis[1-(1, 1-dimethyl-2-propenyl)-1H-indol-3-yl]-3, 6-dihydroxy-2, 5-cyclohexadiene-1, 4-dione and ARQ monoacetate are metabolites from mycelium of Aspergillus terreus IFO 6123. ARQ diacetate was converted into ARQ monoacetate by treatment with 5% aq. NaHCO₃ in pyridine at 80°C for 5 min, and the yield was 93.4%. Similarly, by treatment with 5% aq. NaHCO₃ in acetone at room temperature, 2, 5-diacetoxy-p-xyloquinone and 2, 5-diacetoxy-p-benzoquinone were converted into 2-acetoxy-5-hydroxy-p-xyloquinone (yield, 85.8%) and 2-acetoxy-5-hydroxy-p-benzoquinone (yield, 66.7%), respectively.