Intramolecular Oxidative Coupling of Aromatic Compounds. V. para-para Diphenolic Oxidative Coupling as a Possible Route to the Eupodienone Skeleton

Abstract

The synthesis of (2RS,3RS)-1,4-bis(4-hydroxy-3,5-dimethoxyphenyl)-2,3-dimethylbutan-1-one (9) is described. Diphenolic oxidative coupling of (9) gave the unstable dienone (24), which decomposed in methanol to give what is believed to be the acetal (26). Synthesis of the related diarylbutane (10) was also achieved, but diphenolic coupling gave no useful result. The claimed formation of the bis ( spiro dienone ) (7) on oxidation of 4,4′-(butane-1,4-diyl) bisphenol could not be confirmed.