Synthesis of pancratistatin models

Article abstract of DOI:10.1016/S0040-4039(00)61773-2

Two model syntheses for the phenanthridone core of the cytotoxic alkaloid pancratistatin are reported. The key maneuver in these syntheses is 1,4-addition of an ortho-lithiated benzamide derivative to 1-nitrocyclohexene. The resulting 2-aryl-1-nitrocyclohexanes (6 and 11) are further transformed into the pancratistatin models 2 and 3.