Chemistry of insect antifeedants from Azadirachta indica (Part 17): Synthesis of model compounds of azadirachtin. Unusual effect of remote substituents on the course of the oxidative ring contraction reaction

Article abstract of DOI:10.1016/S0040-4020(01)89292-9

The synthesis of model compounds of azadirachtin containing the tetrahydrofurancarboxylate hemiketal functional group was achieved. The course of the oxidative ring contraction reaction that was used to form this functional group was observed to be unusually sensitive to the nature of substituents remote from the reactive centre.