Stereocontrolled total synthesis of (-)-kainic acid.
[reaction: see text] 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 alpha,beta-unsaturated lactone with high diastereoselectivity. Two alternative protocols for the construction of the alpha,beta-unsaturated lactone were also developed.
Sakaguchi
Hiroshi
H
Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.
Tokuyama
Hidetoshi
H
Fukuyama
Tohru
T
D003500:Cyclization; D005998:Glycine / Q000737:chemistry; D007608:Kainic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D007783:Lactones; D007608:Kainic Acid; D005998:Glycine