Novel Concise Synthesis of (−)‐Clausenamide

A six‐step synthesis of (−)‐clausenamide is described. Optically pure ( R , E )‐1,3‐diphenylallylic alcohol was acetylated and then subjected to an Ireland‐Claisen rearrangement, giving the γ , δ ‐unsaturated acid, which underwent a substrate‐induced stereoselective bromolactonization to afford the expected all‐equatorial substituted bromo‐ δ ‐lactone. An unusual chemo‐selective aminolysis of the lactone resulted in the formation of a γ , δ ‐epoxy‐amide in stereospecific manner. Base‐promoted cyclization of this intermediate and the subsequent Davis oxidation furnished the synthesis, delivering the final product in >99% ee and up to 34% overall yield.