Intramolecular Oxidative Coupling of Aromatic Compounds. I. Oxidation of Diphenolic Substrates

Abstract

The synthesis of (2RS,3SR)-1-(3,5-dihydroxy-4-methoxyphenyl)-(4-hydroxy-3,5-dimethoxy-phenyl)-2,3-dimethylbutan-1-one (26) is described. Diphenolic oxidative coupling of (26) did not produce a eupodienone -type product. An aryltetralin derivative was formed instead by aryl-benzyl coupling and was further oxidized to the novel oxa spiro dienone (63). The acetoxy compound (71) derived by reduction of the carbonyl group in (26) gave a similar product (72).