Total synthesis of (-)-kainic acid via intramolecular Michael addition: a second-generation route.

[摘要]：A total synthesis of (-)-kainic acid (I) starting from the com. available 2-azetidinone is described. The key d-lactone intermediate was concisely prepd. from the com. 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 addn. protocol of a b-amino-d-lactone intermediate with high diastereoselectivity.

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