A concise total synthesis of (−)-γ-lycorane via an aromatic C H alkylation of unactivated secondary alkyl iodide

Abstract A concise and straightforward total synthetic approach towards lycorine-type alkaloid (−)-γ-lycorane has been achieved in 7 steps. The key feature of the route is the employment of a palladium-catalyzed aromatic C H alkylation of unactivated secondary alkyl iodide. The synthetic protocols also involve a palladium-catalyzed deracemization of allylic carbonate, a Johnson-Claisen rearrangement and an iodocyclization.