Tricyclic 6-7-6 and 6-8-6 carbon ring systems are present in numerous biologically active natural molecules. However, simple and efficient synthetic approaches to these scaffolds remain challenging. Herein, we report a versatile strategy for constructing these ring systems via Fe(NO3)3-triggered radical arylation of arenes starting from cyclopropanols. This synthetic utility has been demonstrated in the synthesis of the natural product N-acetylcolchinol-O-methyl ether.