Chemistry: A European Journal 2015-03-02

A short scalable route to (-)-α-kainic acid using Pt-catalyzed direct allylic amination.

Ming Zhang, Kenji Watanabe, Masafumi Tsukamoto, Ryozo Shibuya, Hiroyuki Morimoto, Takashi Ohshima

Index: Chemistry 21(10) , 3937-41, (2015)

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Abstract

An increased supply of scarce or inaccessible natural products is essential for the development of more sophisticated pharmaceutical agents and biological tools, and thus the development of atom-economical, step-economical and scalable processes to access these natural products is in high demand. Herein we report the development of a short, scalable total synthesis of (-)-α-kainic acid, a useful compound in neuropharmacology that is, however, limited in supply from natural resources. The synthesis features sequential platinum-catalyzed direct allylic aminations and thermal ene-cyclization, enabling the gram-scale synthesis of (-)-α-kainic acid in six steps and 34% overall yield.© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.