Concise Total Synthesis of (−)-Vermiculine through a Rhodium-Catalyzed C2-Symmetric Dimerization Strategy

A short and efficient synthesis of the C₂-symmetric antibiotic (−)-vermiculine by utilizing an enantioselective catalytic one-step dimerization methodology as key-step to construct the core structure is reported. The late-stage modifications feature a double metathesis homologation followed by a double Wacker-type oxidation. These key-steps allowed the synthesis of vermiculine in only seven steps, starting from commercially available building blocks.