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.
All Science Journal Classification (ASJC) codes
- Organic Chemistry