Development of methods for the chemical modification of compounds obtained from plant biomass is continued at the ZIOC

Modern production of organic compounds, materials and fuels mainly uses building blocks derived from fossil resources: oil, coal, and natural gas. In recent years, increasing attention has been drawn to the awareness of the need for industry to switch to the use of renewable raw materials, namely plant biomass. Among the most promising approaches is the development of new technologies based on platform chemicals that can be easily obtained by chemical conversion of biomass. One of these structures is 5-hydroxymethylfurfural (5-HMF), which has a huge synthetic potential for obtaining fuels, various materials, and important products of fine organic synthesis.

Scientists of the Laboratory of Metal Complex and Nanoscale Catalysts of the Zelinsky Institute are actively developing new methods for the chemical modification of 5-HMF. In one of their recent studies, they succeeded in realizing a Diels-Alder cascade reaction between 5-HMF dimers as dienes and alkynes as dienophiles. The process goes with exceptional regio- and diastereoselectivity, leading to the formation of 1,4;5,8-diepoxynaphthalenes, valuable intermediates on the way to the synthesis of various biologically active compounds. The reaction pathways were studied in detail using quantum chemical calculations to identify the main factors affecting the selectivity of the process. In the future, it is planned to continue research in this area, aimed at studying the possibility of expanding the range of used dienophiles and regulating the electronic effect of substituents while maintaining the overall reactivity.

Source:

Gleb M. Averochkin, Evgeniy G. Gordeev, Fedor A. Kucherov, Valentine P. Ananikov Rapid access to molecular complexity from bioderived 5-HMF derivatives via cascade cycloadditions // Green Chem., 2023, accepted manuscript. DOI: 10.1039/d2gc04197a.