Stereocontrolled Synthesis of Multisubstituted 1,3-Dienes via an Allene–Claisen RearrangementThis work was partially supported by JSPS KAKENHI (grant numbers JP16H01157 and JP26293004), the Science and Technology Research Promotion Program for Agriculture, Forestry, Fisheries, and Food Industry (M. S.), the NOVARTIS Foundation for the Promotion of Science, the Kurata Memorial Hitachi Science and Technology Foundation (K. M.), and the Cooperative Research Program of the Network Joint Research Center for Materials and Devices
Received: 28 April 2017
Accepted after revision: 03 July 2017
27 July 2017 (eFirst)
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 (1E,3Z)-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.