Sequential One‐Pot Process to Construct a Dual C−C Bond: Synthesis of Fluorenes and Total Synthesis of 4‐ O ‐Demethyl‐nobilone

Abstract Herein, a sequential one‐pot process is described for accessing 9,9‐disubstituted‐9 H ‐fluorenes via the formation of a dual C−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.