Studies on the Chemical Reactivity of the Quinone Methide Derived from the Oxidative Cyclization of α-Methyl-3,4-dihydroxyphenylalanine Ethyl Ester

Article abstract of DOI:10.1021/jo00148a007

Air oxidation of the ethyl ester of (S)-α-methyl-3,4-dihydroxyphenylalanine <(S)-α-MeDopa> generates the corresponding cyclic quinone methide which proved to be unreactive toward nucleophiles.Under a variety of reaction conditions the quinone methide rearranged to an indole, the structure of which was established by an independent synthesis to be ethyl 5,6-dihydroxy-2-methylindole-3-carboxylate.