Directed ortho metalation - Cross coupling connections. Remote lateral metalation - Cyclization of 2-Imino-2'-methyl biaryls to 9- aminophenanthrenes. A synthesis of the alkaloid piperolactam C+

Article abstract of DOI:10.1016/S0040-4039(97)10670-0

2-Imino-2'-methyl biaryls, conveniently available by Suzuki cross coupling protocol, undergo lithium diethyl amide-mediated metalation - cyclization to give 9-aminophonanthrenes (Table 1). The application of this new general methodology to the first synthesis of the alkaloid piperolactam C (9) is described.