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A Unified Strategy for Kainoid Synthesis
Author(s) -
Fujii Masaya,
Yokoshima Satoshi,
Fukuyama Tohru
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201402452
Subject(s) - chemistry , stereocenter , pyrrolidine , acetic acid , ring (chemistry) , stereochemistry , stereoselectivity , claisen rearrangement , aryl , combinatorial chemistry , alkyl , organic chemistry , catalysis , enantioselective synthesis
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.