Diethylaluminum Ethoxide Mediated Stereoselective Diels-Alder Reaction ofα,β-unsaturated Ketones and Acetoxy-1,3-butadienes as Diene Components

Stereoselective Diels-Alder reaction between several α,β-unsaturated ketones and acetoxy-1,3-butadienes is effectively performed by the promotion of diethylaluminum ethoxide under mild conditions. This reaction is successfully applied to the synthesis of optically active bicyclo[6.4.0]dodecanone 9 which corresponds to the BC ring system of 10-deoxy taxane derivatives from the 8-membered ring enone 7 and diene 2.