Concise access to C2-ethylidene pyrrolo[1,4]benzodiazepine natural products

Abstract

A 3-step route toward pyrrolo[1,4]benzodiazepine (PBD) antitumor antibiotic class members oxo-prothracarcin and boseongazepine B has been developed. This methodology also enables preparing oxo-tomaymycin in only 4 linear steps representing the shortest total synthesis known to date. The synthesis features an olefination with sterically demanding Julia–Kocienski reagents as the key step.