A Unified Strategy for Kainoid Synthesis

被引：12

作者：

Fujii, Masaya ^{[1
,2
]}

Yokoshima, Satoshi ^{[1
]}

Fukuyama, Tohru ^{[1
]}

机构：

[1] Nagoya Univ, Grad Sch Pharmaceut Sci, Chikusa Ku, Nagoya, Aichi 4648601, Japan

[2] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 2014卷 / 22期

基金：

日本学术振兴会;

关键词：

Synthesis design; Total synthesis; Natural products; Alkaloids; Cyclization; Rearrangement; ACROMELIC ACID-A; ENOLATE CLAISEN REARRANGEMENT; CONCISE ENANTIOSELECTIVE SYNTHESIS; KUTZING CORSICAN-MOSS; KAINIC ACID; AMINO-ACIDS; FORMAL SYNTHESIS; STEREOCHEMICAL CONTROL; DOMOIC ACID; (-)-ALPHA-KAINIC ACID;

D O I：

10.1002/ejoc.201402452

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：4823 / 4836

页数：14

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