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 <i>ortho</i>-metalation (D<i>o</i>M), a selective demethylation, an <i>ortho</i>-allylation, and an oxidative [3 + 2]-cycloaddition mediated by an iodine­(III) reagent