Diethylaluminum Ethoxide Mediated Stereoselective Diels-Alder Reaction of (alpha),(beta)unsaturated Ketones and Acetoxy-1,3-buta-dienes as Diene Components

Stereoselective Diels-Alder reaction between several (alpha),(beta)unsaturated ketones and acetoxy-l,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.