A Unified Strategy for Kainoid Synthesis
A Unified Strategy for Kainoid Synthesis
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Kainoid 合成的统一策略
DOI：
10.1002/ejoc.201402452
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发表时间：
2014
期刊：
影响因子：
--
通讯作者：
Tohru Fukuyama
中科院分区：
文献类型：
--
作者：
Masaya Fujii;Satoshi Yokoshima;Tohru Fukuyama
发展了一种统一的海人素合成策略。该策略的关键特征包括Claisen-Ireland重排以构建连续的立体中心和具有完全立体选择性的吡咯烷环的钯催化形成。本方案使得能够从常见中间体和适当的乙酸衍生物开始快速获得在吡咯烷环的4-位具有不同类型的取代基（烯基、芳基和烷基）的广泛的kainoids。为了测试该策略的通用性，我们已经分别使用3-甲基丁-3-烯酸、2-（2-甲氧基苯基）乙酸和2-环丙基乙酸完成了红藻氨酸、邻甲氧基苯基衍生物（MFPA）和新型环丙基衍生物（CPKA）的合成。
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.