Eleuthesides and their analogs: III. Reaction of Red-Al with γ,δ-epoxy nitriles

Oxiranyl-substituted cycloalkenecarbonitriles obtained by the Beckmann fragmentation of oximes derived from levoglucosenone adducts with 1,3-butadiene, isoprene, cyclohexadiene, and cyclopentadiene were subjected to Red-Al reduction with opening of the epoxide ring. The reactions with 1,3-butadiene, isoprene, and cyclohexadiene derivatives were accompanied by cyclopropane ring closure and reduction of the cyano group to aldehyde, whereas the cyclopentadiene derivative underwent hydrogenolysis of the oxirane fragment.