Formal Synthesis of Merrilactone A Using a Domino Cyanide 1,4-Addition–Aldol Cyclization

A formal synthesis of merrilactone A has been completed using a domino 1,4-addition–aldol process as the key step. Both iodo- and cyano-1,4-addition–aldol cyclizations were productive in forming the highly hindered C1–C9 bond linking <i>vic</i>-quaternary and tertiary stereocenters. The latter method was used to complete a formal total synthesis of the natural product.