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

Regioselective Domino Metathesis of 7-Oxanorbornenes and Its Application to the Synthesis of Biologically Active Glutamate Analogues
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DOI:
10.1002/ejoc.200800704
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发表时间:
2008-11-01
影响因子:
2.8
通讯作者:
Sasaki, Makoto
Sasaki, Makoto
中科院分区:
化学3区
文献类型:
--
作者:
Ikoma, Minoru;Oikawa, Masato;Sasaki, Makoto

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发展了7-氧杂环丙烷的高区域选择性多米诺异构化反应,该反应利用了分子内酰基与金属Ru的缔合作用。利用该反应,在12-14步中有效地合成了12个由地西赫巴因激发的谷氨酸类似物;其中一个类似物显示出与中枢神经系统抑制相一致的生物活性。((C)Wiley-VCH Verlag GmbH&Co.KGaA,69451,德国温海姆)
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)