Stereoselective formal synthesis of (+)-allokainic acid via thiol-mediated acyl radical cyclization.
Stereoselective formal synthesis of (+)-allokainic acid was accomplished starting from L-glutamate by using a thiol-mediated acyl radical cyclization as a key step. The cyclization of a formylalkenoate proceeded in a highly diastereoselective manner to give trans-4,5-disubstituted pyrrolidin-3-one without the production of the cis-isomer. The pyrrolidinone was then converted into the established synthetic intermediate of (+)-allokainic acid via the iron-catalyzed coupling reaction with an isopropenyl Grignard reagent.
Kyoto University, Japan. yamak@pharm.kyoto-u.ac.jp
Ken-ichi
K
Yamada
Tomohiro
T
Sato
Masaki
M
Hosoi
Yasutomo
Y
Yamamoto
Kiyoshi
K
Tomioka
D003500:Cyclization; D018698:Glutamic Acid / Q000138:chemical synthesis / Q000737:chemistry; D007608:Kainic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis / Q000737:chemistry
D013438:Sulfhydryl Compounds; C495695:allokainic acid; D018698:Glutamic Acid; D007608:Kainic Acid