Journal
HETEROCYCLES
Volume 96, Issue 5, Pages 884-896Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.3987/COM-18-13898
Keywords
Kainic Acid; Samarium Diiodide; Bromoalkyne; Radical Cyclization; Wilkinson Catalyst
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A formal synthesis of (-)-kainic acid (1) starting from the known D-serine derivative 9 has been established in 14 steps. Construction of all the stereogenic centers on the pyrrolidine core of 1 was successfully achieved by application of SmI2-mediated radical cyclization to the alpha,beta-unsaturated ester having an alkyne moiety, followed by hydroxy group directed diastereoselective hydrogenation over Wilkinson's catalyst.
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