Total Synthesis of (±)-Merrilactone A

The total synthesis of racemic merrilactone A (a neurotrophic agent) is described, featuring
simultaneous and stereospecific creation of the C4 and C5 stereocenters via a notable silyloxyfuran Nazarov
cyclization. Full details of the successful synthetic strategy are given, as well as several examples of the
interesting reactivity of intermediates that were prepared and studied during the execution of the total
synthesis. A detailed investigation of the Lewis acid-catalyzed Nazarov cyclization of silyloxyfurans was
conducted, including a systematic study of substrate scope and limitations. In addition, experiments were
conducted that suggest the participation of Lewis acidic silicon species in the Nazarov cyclization.