Total synthesis of spirocyclic fungal metabolites (±)-berkeleyamide D and (±)-azaspirene will be presented. Structural analysis and reported biosynthetic studies of -hydroxy/methoxy--lactam-based natural products prompted us to devise a biomimetic synthetic solution to these natural products. We constructed the key spirocyclic structure via a series of oxidations and cyclizations of biosynthetically relevant linear precursors. Notably, while our streamlined syntheses of berkeleyamide D and azaspirene sought inspiration from its biogenesis, our experimental data on chemical reactivity of biosynthetically relevant precursors conversely provide insights to the biosynthesis of natural products of this family