One-pot synthesis of naphtho[2,3-b]furan-4,9-diones by sequential coupling/ring closure reactions

Article abstract of DOI:10.1016/S0040-4039(96)02462-8

Treatment of 3-phenyliodonio-1,2,3,4-tetrahydronaphthalenides with terminal acetylenes in the presence of a bis(triphynylphosphine)palladium chloride-cuprous iodide catalyst or cuprous oxide in N-methylpiperidine or pyridine, respectively, furnished the corresponding 2-substituted naphtho[2,3-b]furan-4,9-diones in moderate to good yields. The utility of this method was demonstrated in the synthesis of a cytotoxic natural product, 2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione.