Abstract
An investigation of the reaction of tryptophan and its methyl ester with ninhydrin has been conducted. In the reaction of tryptophan with ninhydrin only one product, yohimbanone ( 1 ), is isolated. In contrast, an intermediate, Pictet–Spengler product 3 , is isolated from the reaction of tryptophan methyl ester with ninhydrin. The isolation of this intermediate provides support for a proposed mechanism of this novel rearrangement, which is presented herein.
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