A stereocontrolled total synthesis of (-)-kainic acid is described. A fully functionalized trisubstituted pyrrolidine ring was constructed by ring-closing metathesis of an acrylate derivative followed by an intramolecular Michael addition of the resultant α,β-unsaturated lactone with high diastereoselectivity. Two alternative protocols for the construction of the α,β-unsaturated lactone were also developed.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry