Synthesis of highly functionalized biologically active molecules utilizing a cascade cyclization of propargylic esters

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It is known that propargylic esters react with palladium complex leading to propargylpalladium complexes, which further cause various transformations in the presence of soft nucleophiles to produce the corresponding products. Among them, palladium-catalyzed cyclization of propargylic esters with bis-nucleophiles is one of the useful methodologies for the construction of functionalized cyclic molecules in one step. In this study, we examined the synthesis of highly functionalized heterocyclic molecules by the palladium-catalyzed reactions of propargylic esters with bis-nucleophiles. As the result, our effort has led to the development of 1) the synthesis of tetrasubstituted furans by a reaction of propargyl keto esters and 2) the synthesis of furo[3,2-c]pyran-4-one derivatives by a reaction of propargyl carbonates with 4-hydroxy-2-pyrones.