Herein, a sequential one-pot process is described for accessing 9,9-disubstituted-9H-fluorenes via the formation of a dual CÀ C bond, and this protocol is successfully extended to the total synthesis of the naturally occurring 4-O-demethyl-nobilone. The overall process proceeds via Suzuki coupling between ortho-bromobenzylic(tertiary) alcohols and arylboronic acids, followed by zinc(II) iodide-mediated intramolecular cyclization reactions. The strategy has been applied to an inclusive range of substitutions over ortho-bromobenzylic(tertiary) alcohols and arylboronic acids.