geometries of the proposed ortho-benzene mimics F-H deviate significantly from that of ortho-subs tuted benzenes with in-plane topology of the subs tuents. In our study, we focused on the tricyclo[3.3.0.0 ]octane (bisnoradamantane or stellane) core I, as preliminary modeling studies revealed that the 1,5-disubs tu on of this cage scaffold exhibits an almost ideal geometry for ortho-subs tuted benzene. Given that the key building blocks for the func onaliza on of previous examples of benzene mimics (cores A-C and F) were corresponding diesters, we focused on the corresponding stellane deriva ve 1 as a main target. At first glance, Camps' group described a promising approach over 40 years ago for the synthesis of compound 1 based on lithia on/I2mediated oxida on of dimethyl octahydropentalene-2,5-dicarboxylate 2 . However, the problema c scaleup and challenging purifica on hampers further study of stellanes. In light of the unreliable reproducibility of the literature synthe c protocol for stellane core assembly and the growing interest in benzene mimics research, we aimed to conduct a detailed study targe ng large-scale prepara on of 1 as star ng material in various medicinal chemistry programs. To achieve the goal addi onal mechanis c understanding of the key steps was needed.