Total Synthesis of Benzofuran-Based Aspergillusene B via Halogenative Aromatization of Enones

A novel “non-aromatic pool” synthetic strategy for the synthesis of benzofuran-based natural products via oxidative haloaromatization of enones is reported. This approach is successfully applied in the first total synthesis of the natural product aspergillusene B. In comparison with a separately executed “aromatic pool” synthesis, the “non-aromatic pool” protocol demonstrates equivalent efficiency but offers a much higher degree of modularity.