Dpto. Química Orgánica, Facultad de C. Químicas, Universidad de Salamanca, Plaza de los Caídos1-5, Salamanca 37008, Spain
Abstract:
The synthesis of the 12-acetoxy enone 15 related to the limonoid azadiradione has been achieved in 12 steps (16% overall yield) starting from tricyclic diester 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.