Two syntheses of (-)-kainic acid via highly stereoselective zinc-ene cyclizations.
Two concise, high-yielding syntheses of enantioenriched (-)-kainic acid are presented. Both routes feature a Pd-catalyzed Zn-ene cyclization that proceeds with complete diastereoselectivity. The key step can be carried out on a multigram scale, and the overall yields are among the highest to date for this marine alkaloid.
Chalker
Justin M
JM
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA. justin.chalker@chem.ox.ac.uk
Yang
Ao
A
Deng
Kai
K
Cohen
Theodore
T
D002712:Chlorides / Q000737:chemistry; D003500:Cyclization; D007608:Kainic Acid / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry; D017967:Zinc Compounds / Q000737:chemistry*
D002712:Chlorides; D013450:Sulfones; D017967:Zinc Compounds; D010165:Palladium; D007608:Kainic Acid