Total Synthesis of (±)-Merrilactone A via Catalytic Nazarov Cyclization

Abstract

The total synthesis of merrilactone A (a neurotrophic agent) has been achieved. In the approach reported, simultaneous creation of the C-4 and C-5 stereocenters was accomplished stereospecifically using an unprecedented variant of the Nazarov cyclization. Additional studies focused upon this Lewis acid-catalyzed cyclization of a silyloxyfuran-containing intermediate are presented.