M. Kirihata, T. Kaziwara, Y. Kawashima, I. Ichimoto
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An Efficient Synthesis of (±)-α-Kainic Acid Using a 3-HydroxyalIylglycine Derivative as a Common Building Block
( + )-α-Kainic acid (1) was synthesized by starting from a building block, N-Boc-3-acetoxyallylglycine ethyl ester (2). The key intermediate, a methyl 4-[(tert-butoxycarbonyl)prenylamino]-5-hydroxy-2-pentenoate derivative (9), was prepared from 2 in eight synthetic steps. After converting 10 into a methyl ester (11), intramolecular ene-carbocyclization of 11 gave a pyrrolidine derivative (12), which was converted to 1 in a moderate yield.
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