Cyclization of m-cresol (I) with ethyl 2-oxocyclohexanecarboxylate (II) in H2SO4 afforded tricyclic benzopyranone (III). This was treated with MeMgBr in boiling anisole to provide the tricyclic dimethylbenzopyran (IV). Dehydrogenation of (IV) using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone gave dibenzopyran (V), which by further bromination with N-bromosuccinimide and 2,2'-azobis(4-methoxy-2,4-dimethylvaleronitrile) produced bromide (VI). Finally, N-alkylation of 4-(3-indolyl)butyric acid (VII) with bromide (VI) in the presence of two equivalents of NaH yielded the title compound.