The total synthesis of (±)-azaspirene was achieved in a total of six steps from commercially available materials. Keys to the conciseness of our synthetic approach were the effective γ-lactam formation from linear precursor and successful tandem epoxidations of γ-lactam to afford α,β-epoxy-γ-hydroxy-γ-lactam intermediate. While our streamlined synthesis of azaspirene sought inspiration from its biogenetic hypothesis, experimentally observed chemical reactivity of biosynthetically relevant precursors conversely provides insights to the biological origin of this natural product.