Gold(I)-Catalyzed Furan-yne Cyclizations Involving 1,2-Rearrangement: Efficient Synthesis of Functionalized 1-Naphthols and Its Application to the Synthesis of Wailupemycin G

Gold-catalyzed cascade cyclization/ 1,2-rearrangement of 1-(2-furanyl)phenyl propargyl alcohols has been developed, which provides a rapid and efficient access to multisubstituted 1-naphthols bearing an enal or enone moiety with high stereoselectivity. The (Z)- or (E)-stereochemistry can be easily controlled by choosing protected- or non-protected substrates. The utility of the methodology has been illustrated in the first total synthesis of wailupemycin G.