Biomimetic Synthesis of (±)-Merochlorin B

A short total synthesis, guided by biosynthetic considerations, of racemic merochlorin B is presented. The formation of its isomer, merochlorin A, was not observed under the conditions. Key steps include a directed ortho-metalation (DoM), a selective demethylation, an ortho-allylation, and an oxidative [3 + 2] -cycloaddition mediated by an iodine(III) reagent.