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Formation of yohimbanones via a novel rearrangement

✍ Scribed by Michael S Leonard; Diane B Hauze; Patrick J Carroll; Madeleine M Joullié

Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
161 KB
Volume
59
Category
Article
ISSN
0040-4020

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✦ Synopsis

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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