4.8 Article

Total Synthesis of (-)-(α)-Kainic Acid via a Diastereoselective Intramolecular [3+2] Cycloaddition Reaction of an Aryl Cyclopropyl Ketone with an Alkyne

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卷 14, 期 10, 页码 2540-2543

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AMER CHEMICAL SOC
DOI: 10.1021/ol3008414

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  1. National Science & Technology Major Project Key New Drug Creation and Manufacturing Program, China [2009ZX09102-026]

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An enantioselective synthesis of (-)-(alpha)-kainic acid in 15 steps with an overall yield of 24% is reported. The pyrrolidine kainoid precursor with the required C2/C3 trans stereochemistry was prepared with complete diastereoselectivity via an unprecedented SmI2-catalyzed intramolecular [3 + 2] cycloaddition reaction of an aryl cyclopropyl ketone and an alkyne. Double bond isomerization was then employed to set the remaining stereochemistry at the C4 position en route to (-)-(alpha)-kainic acid.

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