Asymmetric total synthesis of (-)-alpha-kainic acid using an enantioselective, metal-promoted ene cyclization.
[figure: see text] 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.
Xia
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Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, USA.
Ganem
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D018690:Excitatory Amino Acid Agonists / Q000138:chemical synthesis*; D007608:Kainic Acid / Q000138:chemical synthesis*; D007769:Lactams / Q000737:chemistry; D008274:Magnesium / Q000737:chemistry; D013237:Stereoisomerism; D015032:Zinc / Q000737:chemistry; D015040:Zirconium / Q000737:chemistry
D018690:Excitatory Amino Acid Agonists; D007769:Lactams; D015040:Zirconium; D008274:Magnesium; D015032:Zinc; D007608:Kainic Acid