Versatile Synthesis of rac‐ and meso‐Hydroxymethyl Cyclohexenoids Containing Phenyl Groups: α‐/β‐Glucosidase Activities, Inhibition Kinetics and Molecular Docking Studies

The effective strategy has been developed to synthesize a series of monophenyl and diphenyl carbasugar analogues, from the cycloadduct reaction of furan and maleic anhydride, containing halogen groups based on the conduritol scaffold. The strategy mainly consists of reduction, esterification, bromination, formation of new double bond and replacement of bromine with phenyl by Suzuki coupling reaction. New phenyl‐substituted carbasugars were obtained by cleavage of the oxo bridge and subsequent hydrolysis of the esters. The structures of the target compounds were defined using different chemical methods. In vitro inhibitory activity studies, kinetic and molecular docking studies were performed against α‐, β‐glucosidase enzymes for the final compounds. This work describes protocols that provide access to valuable phenyl‐substituted carba sugars trhough i) addition of maleic anhydride to furana, ii) reduction of carbonyl group, iii) double bond bromination and elimination iv) bromine exchange with phenyl v) oxo‐bridge opening.