First Total Synthesis of Viridistratin B

A total synthesis of viridistratin B, a non-alternant polycyclic aromatic hydrocarbon (PAH) natural product featuring a benzo[j]fluoranthene framework, has been accomplished in an eight-step linear sequence with a 17% overall yield. The key features of our synthesis include a concise route to the tetracyclic cyclization precursor, a metal-free construction of benzo[j] fluoranthene core via a microwave-assisted intramolecular [2+2]/retro-[2+2] cycloadditions of the bis-N-tosylhydrazone and a regioselective O-demethylation.