Stereocontrolled Synthesis of Multisubstituted 1,3-Dienes via an Allene–Claisen Rearrangement

We herein developed a stereoselective synthetic method for the preparation of multisubstituted 1,3-dienes via an allene–Claisen rearrangement. The Claisen rearrangement of anti -allenyl alcohols provided (1 E ,3 Z )-1,3-dienes, which are essential components of bongkrekic acid, in high stereoselectivities. To demonstrate the synthetic utility of the resulting 1,3-dienes, further functional transformations and Diels–Alder reactions are described.