Density Functional Theory Mechanistic Study of the Regioselectivity of 1,3-Dipolar Cycloaddition Reaction Between Acyclic Nitrones and Norsarkomycin and its Analogues

The 1,3-dipolar cycloaddition reaction (1,3-DC) has offered the opportunity to produce a wide range of heterocyclic compounds [1,2]. These compounds were used to prepare new molecules of crucial importance for both pharmaceutics and industry sector [3]. The application of 1,3-DC reactions in natural product synthesis is heavily dependent upon an understanding of the regioselectivity and chemioselectivity of the reaction. The regioselectivity of 1,3-dipolar cycloaddition reactions can be determined by electronic structure of reactants, steric factors or combination of both effects [4]. The aim of this work is to determine the preferred regioisomer (ortho/meta) of the 1,3-cycloaddition reaction between acyclic nitrones and norsarkomycin and its analogues. The effects of N-substituents nitrones on the reactivity of the reaction have been evaluated by global, local reactivity and activation energy.