Scientists of the Zelinsky Institute continue research in the field of asymmetric organocatalysis

Kojic acid is a natural compound produced by a number fungi, notably Aspergillus oryzae. This molecule and its synthetic derivatives exhibit a wide range of biological activities: antiviral, anticancer, antioxidant, and bactericidal.

Scientists of the I.N. Nazarov Laboratory of Fine Organic Synthesis of the Zelinsky Institute does active research in the field of asymmetric synthesis of chiral derivatives of kojic acid. In their latest study, they succeeded in developing a new asymmetric process for the double addition of kojic acid derivatives to 2-nitroallyl carbonates. As a result of the reaction with high enantioselectivity, nitro compounds with two hydroxypyranone fragments are formed, which are inaccessible by other methods. A number of synthetic transformations involving the obtained structures made it possible to synthesize chiral nitroglutarates, promising precursors of enantiomerically pure derivatives of aminoglutaric acid.

Source:

Ruslan A. Kovalevsky, Maxim V. Smirnov, Alexander S. Kucherenko, Kseniya A. Bykova, Elizaveta V. Shikina, Sergei G. Zlotin Organocatalytic Asymmetric Double Addition of Kojic Acids to 2-Nitroallylic Carbonates Eur. J. Org. Chem. 2022, e202101435. DOI: 10.1002/ejoc.202101435.