Journal
ORGANIC LETTERS
Volume 14, Issue 10, Pages 2540-2543Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol3008414
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Funding
- 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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