Synthetic and Mechanistic Studies of the Retro-Claisen Rearrangement 4. An Application to the Total Synthesis of (+)-Laurenyne

A novel asymmetric total synthesis of marine natural product (+)-Laurenyne has been achieved. The key elements of the strategy are the sequential metal ion-templated SN2‘ cyclization affording a highly functionalized chiral vinyl cyclobutane and a retro-Claisen rearrangement for the construction of an eight-membered ring ether.