Racemic Total Synthesis of Elmonin and Pratenone A, fromStreptomyces, Using a Common Intermediate Prepared byperi-Directed C–H Functionalization

The first total synthesis of elmonin and pratenone A, two complex rearranged angucyclinones from Streptomyces, is reported. Using peri-directed C-H functionalization, the key naphthalene fragment present in both synthetic targets was efficiently prepared. Coupling to two anisole-derived fragments gave access to the natural products, in which elmonin was prepared using a biomimetic spiro-ketalization.