Model insect antifeedants. Synthesis of azadiradione fragments through acyl radicals cyclizations and stannane coupling reactions

Article abstract of DOI:10.1016/0040-4020(96)00149-4

A diastereoselective and versatile synthesis of the model insect antifeedant 16 related to azadiradione has been achieved in nine steps starting from α-cyclocitral 1. The key steps involve intramolecular alkene addition of an acyl radical and a Stille coupling reaction of a vinyl iodide with a stannylfuran.