Stereoselective Total Synthesis of Carolacton

A short and convergent strategy for the stereoselective total synthesis of biologically active natural product carolacton has been accomplished. Our synthesis highlights the Urpi acetal aldol, Crimmins aldol, Ireland–Claisen rearrangement, TiCl4-assisted aldol followed by β-hydroxy elimination to construct C7–C8 olefin, and ring-closing metathesis as the key steps for achieving the target molecule with an overall yield of 18.8%.