132785-33-2Relevant 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.
Diastereo- And enantioselective conjugate addition of α-ketoesters to nitroalkenes catalyzed by a chiral Ni(OAc)2 complex under mild conditions
Nakamura, Ayako,Lectard, Sylvain,Hashlzurne, Daisuke,Hamashima, Yoshitaka,Sodeoka, Mikiko
supporting information; experimental part, p. 4036 - 4037 (2010/05/01)
(Figure Presented) A highly efficient, catalytic, dlastereo- and enantloselectlve conjugate addition of a-ketoesters to nltroalkenes has been devised. The reaction was applicable to various substrates. Notably, the combination of endogenous and exogenous bases was effective, allowing a small amount of the catalyst (0.1 -1 mol % NI) to promote the reaction efficiently. The synthetic utility of this reaction was demonstrated In the synthesis of substituted pyrrolidine derivatives, whose stereochemistry Is closely related to biologically Important natural products such as kainic add. Copyright
Towards a versatile synthesis of kainoids II: Two methods for establishment of C-4 stereochemistry
Baldwin, Jack E.,Bamford, Samantha J.,Fryer, Andrew M.,Rudolph, Martin P. W.,Wood, Mark E.
, p. 5255 - 5272 (2007/10/03)
Benzylic lactone hydrogenolysis and enamide reduction were used to generate protected C-4 aryl substituted kainoid analogues which were deprotected to their corresponding free amino acids. X-ray crystographic data were obtained for the C-4 2-MeOPh- analogue.
