Asymmetric synthesis of isohaliclorensin, a key intermediate of bisquinolinylpyrrole alkaloid halitulin

Abstract A new enantioselective total synthesis of N -(3′-aminopropyl)-3-methylazacyclodecane, a partial structure of halitulin, has been achieved in eight steps with 14% overall yield. The key steps are the photochemical ring-expansion reaction of spirooxaziridine to lactam for constructing the azacyclodecane moiety and 1,4-stereoinductive methylation of the resulting lactam.