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

✍ Scribed by Kazuhiro Kobayashi; Tomokazu Uneda; Masataka Kawakita; Osamu Morikawa; Hisatoshi Konishi

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 239 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(96)02462-8

✦ Synopsis

Treatment of 3-phenyliodonio-t,2,4-trioxo-1,2,3,4-tetrahydronaphthalenides with terminal acetylenes in the presence of a bis(triphenylphosphine)palladium chloride-enprous iodide catalyst or cuprous oxide m N-methylpiperidine or pyridine, respectively, furnished the corresponding 2-suhstituled naphlho[2,3-b]furan-4,9q~iones in moderate to good yields. The utility of this method was demonstrated in the synthesis of a cytotoxie natural product, 2-(l-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione.