Studies on the chemical reactivity of the quinone methide derived from the oxidative cyclization of. alpha.-methyl-3, 4-dihydroxyphenylalanine ethyl ester

…, AT Shulgin, N Castagnoli Jr

Index: Cheng, Alice C.; Shulgin, Alexander T.; Castagnoli, Neal Journal of Organic Chemistry, 1982 , vol. 47, # 27 p. 5258 - 5262

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Citation Number: 15

Abstract

Air oxidation of the ethyl ester of (S)-a-methyl-3, 4-dihydroxyphenylalanine[(S)-a-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.