Preparation of the 4-hydroxytryptamine scaffold via palladium-catalyzed cyclization: a practical and versatile synthesis of psilocin.

[reaction: see text] The 4-hydroxytryptamine scaffold of psilocin was successfully prepared via palladium-catalyzed cyclization of protected N-tert-butoxycarbonyl-2-iodo-3-methoxyaniline and an appropriately substituted silyl acetylene. Removal of the protecting groups afforded psilocin in good yield.