Endogenous alkaloids in man, IX. Potential tryptophan‐derived alkaloids in chloral‐treated patients: Synthesis and stereostructure

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Abstract
The trichlorotetrahydroharmancarboxylic acids 5a and 5b were shown to be formed in aqueous medium under neutral, physiological conditions from the amino acid tryptophan and the nonnatural aldehyde chloral. Preparative diastereomer resolution and configurational analysis were performed via the methyl esters 7a/7b. The structure of 7b was proved by an X‐ray structural analysis. By cautious hydrolysis, the chloral‐derived potential „mammalian alkaloids”︁ 5a and 5b were obtained in analytically pure form.