We targeted the synthesis of a potentially 6-or 10-electron homoaromatic homoannulene 6 with a barbaralone-derived framework (Fig. , bottom). For the related bridged aromatic annulenes , semibullvalenes and elassovalene 20 3 (Fig. , top), Vogel had emanated from tetrahydronaphthalenes 7 or hexahydroanthracenes, respectively, employing the central alkene(s) of hydrogenated polyaromatic compounds such as tetrahydronaphthalene as synthetic linchpin for a key cyclopropanation (Fig. , inside → outside). We envisioned an orthogonal approach (outside → inside), utilizing first the outer disubstituted alkene of the related dihydronaphthalene 8, leaving the benzene ring untouched.