An efficient synthesis of the kynurenamines K 1 and K 2 , the major brain and antioxidant metabolites of melatonin 1 is described. Regioselective lithiation of tert-butyl(4-methoxyphenyl) carbamate and iodination provided the (2-iodoaryl)carbamate which when coupled with N-acetyl-propargylamine underwent a Sonogashira reaction. Simultaneous alkyne hydration and Nformylation produced K 2 , whereas alkyne hydration only, produced K 2 .

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The chemistry concerning the most recent syntheses of melatonin (Nacetyl-5-methoxytryptamine) is described.

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