Regioselective Domino Metathesis of 7-Oxanorbornenes and Its Application to the Synthesis of Biologically Active Glutamate Analogues

被引：35

作者：

Ikoma, Minoru ^{[1
]}

Oikawa, Masato ^{[1
]}

Gill, Martin B. ^{[2
]}

Swanson, Geoffrey T. ^{[2
]}

Sakai, Ryuichi ^{[3
]}

Shimamoto, Keiko ^{[4
]}

Sasaki, Makoto ^{[1
]}

机构：

[1] Tohoku Univ, Grad Sch Life Sci, Aoba Ku, Sendai, Miyagi 9818555, Japan

[2] Northwestern Univ, Feinberg Sch Med, Dept Biol Chem & Mol Pharmacol, Chicago, IL 60611 USA

[3] Hokkaido Univ, Grad Sch Fisheries Sci, Hakodate, Hokkaido 0418611, Japan

[4] Suntory Inst Bioorgan Res, Osaka 6188503, Japan

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2008年 / 2008卷 / 31期

基金：

日本学术振兴会;

关键词：

Nitrogen heterocycles; Oxygen heterocycles; Combinatorial chemistry; Domino reactions; Metathesis; Regioselectivity;

D O I：

10.1002/ejoc.200800704

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly regioselective domino metathesis reaction of 7-oxanorbornene was developed that employed an intramolecular association of an amide carbonyl group to a ruthenium metal centre. By using this reaction, twelve glutamate analogues inspired by dysiherbaine were efficiently synthesized over 12-14 steps; one of the analogues exhibited bioactivity consistent with central nervous system depression. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

引用

页码：5215 / 5220

页数：6

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