A total synthesis of (-)-kainic acid starting from the commercially available 2-azetidinone is described. The key δ-lactone intermediate was concisely prepared from the commercially available azetidinone through the Reformatsky-type reaction and an introduction of a glycine moiety. The construction of the functionalized pyrrolidine ring was executed by a one-pot sequential elimination-Michael addition protocol of a β-amino-δ- lactone intermediate with high diastereoselectivity.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry