4.8 Article

Short Total Synthesis of (-)-Kainic Acid

Journal

ORGANIC LETTERS
Volume 16, Issue 9, Pages 2550-2553

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/ol5009526

Keywords

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Funding

  1. Yamada Science Foundation
  2. Ministry of Education, Culture, Sports, Science and Technology (MEXT) [23102009]
  3. Japan Society for the Promotion of Science (KAKENHI) [23228001, 25282233]
  4. Grants-in-Aid for Scientific Research [25282233, 23102009, 23228001] Funding Source: KAKEN

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A short total synthesis of (-)-kainic acid has been developed involving a novel diastereofacial differentiating Cu-catalyzed Michael addition-cyclization reaction, which provided access to a chiral pyrroline in a highly stereoselective manner. The chiral pyrroline was converted to (-)-kainic acid via the stereoselective 1,4-reduction of the pyrroline double bond in three steps.

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