1630067-81-0Relevant articles and documents
A unified strategy for kainoid synthesis
Fujii, Masaya,Yokoshima, Satoshi,Fukuyama, Tohru
, p. 4823 - 4836 (2014/08/05)
A unified strategy for kainoid synthesis was developed. The key features of the strategy involve a Claisen-Ireland rearrangement to construct the contiguous stereogenic centers and a palladium-catalyzed formation of the pyrrolidine ring with complete stereoselectivity. The present protocol has enabled rapid access to a wide range of kainoids with diverse types of substituents (alkenyl, aryl, and alkyl groups) at the 4-position of the pyrrolidine ring, starting from the common intermediate and appropriate acetic acid derivatives. To test the generality of the strategy, we have accomplished the syntheses of kainic acid, o-methoxyphenyl derivative (MFPA), and a novel cyclopropyl derivative (CPKA), using 3-methylbut-3-enoic acid, 2-(2-methoxyphenyl)acetic acid, and 2-cyclopropylacetic acid, respectively.