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Rhodium-Catalyzed Coordination-Assisted Regioselective and Migratory Three-Point Double Annulation of o-Alkenyl Phenols with Tertiary Propargyl Alcohols.

We disclose herein a Rh(III)-catalyzed migratory three-point double annulation of o-alkenyl phenols with propargyl alcohols for de novo construction of naphtho furan derivatives in a regio- and chemoselective manner. The protocol orchestrates two new rings with four new bonds in one operation without the need for any additive. Necessary labeled and control experiments are conducted to elucidate the reaction mechanism. A tertiary hydroxyl group is found to be crucial both for controlling the regioselective insertion of alkyne through chelation with rhodium to form a key spiro cyclic intermediate and for forcing ring expansion via unusual and selective olefin reshuffling, apart from forming an extra (furan) ring. The protocol is scalable and shows tolerance for late stage functionalization of natural products.