Asymmetric Total Synthesis of (−)-α-Kainic Acid Using an Enantioselective, Metal-Promoted Ene Cyclization
journal contributionposted on 12.01.2001, 00:00 by Qian Xia, Bruce Ganem
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A short and efficient asymmetric total synthesis of the title compound 1, which is an important neurotransmitter, has been achieved. The synthesis features a metal-promoted, enantioselective ene reaction that provides entry into the kainic acid ring system from very simple precursors. Moreover, the zirconium-mediated Strecker reaction, which represents an outgrowth of earlier amide-to-imine methodology developed in our laboratory, demonstrates remarkable chemoselectivity and stereoselectivity.