An Improved Synthesis of Canthin-6-one

Kevin M. Czerwinski Department of Chemistry, University of Wisconsin-Stevens Point, Stevens Point, Wisconsin, USACorrespondence[email protected]

Craig A. Zificsak Department of Chemistry, University of Wisconsin-Stevens Point, Stevens Point, Wisconsin, USA

John Stevens Department of Chemistry, University of Wisconsin-Stevens Point, Stevens Point, Wisconsin, USA

Melissa Oberbeck Department of Chemistry, University of Wisconsin-Stevens Point, Stevens Point, Wisconsin, USA

Christopher Randlett Department of Chemistry, University of Wisconsin-Stevens Point, Stevens Point, Wisconsin, USA

Melissa King Department of Chemistry, University of Wisconsin-Stevens Point, Stevens Point, Wisconsin, USA

Steve Mennen Department of Chemistry, University of Wisconsin-Stevens Point, Stevens Point, Wisconsin, USA

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Abstract

An improved route has been devised which provides canthin-6-one in the highest yield from tryptamine to date. Tryptamine is converted to N_b -benzyltryptamine via reaction with benzoylchloride and reduction using LAH. Pictet-Spengler condensation with 2-ketoglutaric acid, removal of the protecting group by CTH, and aromatization with MnO₂ affords canthin-6-one in 48% overall yield.

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An Improved Synthesis of Canthin-6-one

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An Improved Synthesis of Canthin-6-one

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