A Short Scalable Route to (-)-alpha-Kainic Acid Using Pt-Catalyzed Direct Allylic Amination

作者：Zhang Ming; Watanabe Kenji; Tsukamoto Masafumi; Shibuya Ryozo; Morimoto Hiroyuki; Ohshima Takashi^*

来源：Chemistry - A European Journal, 2015, 21(10): 3937-3941.

DOI：10.1002/chem.201406557

• allylic amination
• amino acids
• homogeneous catalysis
• platinum
• total synthesis

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 (-)-alpha-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 (-)-alpha-kainic acid in six steps and 34% overall yield.

• 出版日期2015-3-2