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Paper | Regular issue | Vol 96, No. 5, 2018, pp.882-894
Published online, 26th April, 2018
DOI: 10.3987/COM-18-13898
A Formal Synthesis of (–)-Kainic Acid by Means of SmI2-Mediated Radical Cyclization

Kazunori Takahashi,* Takumi Ito, Wataru Yamada, Masayoshi Tsubuki, and Toshio Honda

*Institute of Medicinal Chemistry, Hoshi University, Ebara 2-4-41, Shinagawa-ku, Tokyo 142-8501, Japan


A formal synthesis of (–)-kainic acid (1) starting from the known D-serine derivative 9 has been established in 14 steps. Construction of all the stereogenic centers on the pyrrolidine core of 1 was successfully achieved by application of SmI2-mediated radical cyclization to the α,β-unsaturated ester having an alkyne moiety, followed by hydroxy group directed diastereoselective hydrogenation over Wilkinson’s catalyst.