Synthesis of 1,2,3,12a,12b-Hexahydrocyclopropa-[1,2-d]benzo[f]pyrrolo[1,2-b]isoquinolin-5,7-dione related to duocarmycins and anthramycin

Structural features of the Duocarmycins and Anthramycin were incorporated into 1,2,3,12a,12b-hexahydro-cyclopropa[1,2-d]benzo[f]pyrrolo[1,2-b]isoquinolin 5,7-dione. The synthesis of the cis and trans diastereomers was accomplished using a benzyne Diels-Alder reaction and an imine-anhydride cyclization as key steps.