Synthesis of CC-1065 and duocarmycin analogs via intramolecular aryl radical cyclization of a tethered vinyl chloride

Article abstract of DOI:10.1016/S0040-4039(98)00232-9

The 5-exo-trig radical cyclization of an aryl halide onto a tethered vinyl chloride produces the 3-chloromethyl dihydroindole precursors for CC- 1065 and duocarmycin analogs with chlorine installed as a suitable leaving group for subsequent cyclopropane spirocyclization. The generality of this approach was examined in the context of six CC-1065 and duocarmycin analogs previously synthesized in this laboratory.