Synthesis of a CDE Fragment of the Insect Antifeedant 12-Hydroxyazadiradione

Abstract

A diastereoselective and versatile synthesis of the model insect antifeedant 23 related to 12-hydroxyazadiradione has been achieved in 11 steps starting from α-cyclocitral, 1. The key steps involve intramolecular 1,3-dipolar cycloaddition of a nitrile oxide and a Stille coupling reaction of a vinyl iodide with a stannylfuran.