The synthesis and reactions of tropan-3-yl-2- and -3-indoles, abbreviated congeners of the psychoactive alkaloid ibogaine, are described. An unusual isomerization of 2-substituted indoles was investigated using computational and spectroscopic techniques. The work provides synthetic routes to these compounds and characterizes the isomerization process, contributing to the chemistry of axial and atropisomeric chirality in alkaloid synthesis.
Psilocin and psilocybin, two hallucinogenic indoles, were analyzed using a combined gas-liquid chromatography–mass spectrometry technique after conversion to their trimethylsilyl derivatives. The method was applied to an extract of the mushroom Psilocybe cubensis (Earle) Sing., enabling detection and identification of both compounds.
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