Total synthesis of (-)-kainic acid via intramolecular Michael addition: a second-generation route.
A total synthesis of (-)-kainic acid starting from the commercially available 2-azetidinone is described. The key delta-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 beta-amino-delta-lactone intermediate with high diastereoselectivity.
Sakaguchi
Hiroshi
H
Graduate School of Pharaceutical Sciences, University of Tokyo, Tokyo, Japan.
Tokuyama
Hidetoshi
H
Fukuyama
Tohru
T
D001384:Azetidines / Q000737:chemistry; D056890:Eukaryota / Q000737:chemistry; D007608:Kainic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D011759:Pyrrolidines / Q000737:chemistry; D013237:Stereoisomerism
C116379:2-azetidinone; D001384:Azetidines; D007783:Lactones; D011759:Pyrrolidines; C032519:pyrrolidine; D007608:Kainic Acid