Enantioselective total synthesis of (-)-alpha-kainic acid.
An enantioselective total synthesis of (-)-alpha-kainic acid is described. Key steps are an Ir-catalyzed allylic amination with a propargylic amine to provide an enyne and a diastereoselective intramolecular Pauson-Khand reaction. Subsequent steps involve a Baeyer-Villiger reaction, reduction of the resulting lactone, and direct Jones oxidation of a silyl ether.
Farwick
Andreas
A
Organisch-Chemisches Institut der Ruprecht-Karls-Universität Heidelberg, Im Neuenheimer Feld 270, D-69120 Heidelberg, Germany.
Helmchen
Günter
G
D000586:Amination; D002384:Catalysis; D006865:Hydrogenation; D007495:Iridium / Q000737:chemistry; D007608:Kainic Acid / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity
D007495:Iridium; D007608:Kainic Acid