Rhodium(III)‐catalyzed double C−H annulation of 3‐(acetylamino)coumarins with internal arylacetylenes is reported. The reaction proceeds smoothly accompanied by two C−C and two C−N bond formation to produce 8‐aryl‐6H‐chromeno[4’,3’:4,5]pyrrolo[2,1‐a]isoquinolin‐6‐ones selectively. It also provides a straightforward route to natural product inspired pentacyclic pyrrolocoumarin derivatives from readily available building blocks.