Efficient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids-first total syntheses of O-methylmurrayamine A and 7-methoxv murray acine, first asymmetric synthesis and assignment of the absolute configuration of (-)-trans-dihydroxygirinimbine

摘要

Iron-mediated oxidative cyclisation provides an efficient approach to pyrano[3,2-a]carbazole alkaloids. Thus, improved routes to girinimbine and murrayacine as well as the first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine are reported. Asymmetric epoxidation of girinimbine led to (-)-frans-dihydroxygirinimbine and the assignment of its absolute configuration.