Phenol oxidation and biosynthesis. Part 27. Reactions of relevance to the formation of erysodienone in vitro

Abstract

Potassium hexacyanoferrate(III) oxidation of N-(2-arylethyl)-2-arylacetamide and arylmethyl arylpropyl ketone gave the corresponding nine-membered ring derivatives formed by p,p-phenol oxidative coupling (where aryl was 3-hydroxy-4-methoxyphenyl). This strongly supports the previously reported mechanism for the in vitro formation of erysodienone. The required ketone was prepared from O-benzylisovanillin by homologation with toluene-4-sulphonylmethyl isonitrile.