7-氧杂降冰片烯的区域选择性多米诺复分解反应及其在生物活性谷氨酸类似物合成中的应用
Regioselective Domino Metathesis of 7-Oxanorbornenes and Its Application to the Synthesis of Biologically Active Glutamate Analogues.
作者信息
Ikoma Minoru, Oikawa Masato, Gill Martin B, Swanson Geoffrey T, Sakai Ryuichi, Shimamoto Keiko, Sasaki Makoto
机构信息
Graduate School of Life Sciences, Tohoku University, Aoba-ku, Sendai 981-8555, Japan, , E-mail:
出版信息
European J Org Chem. 2008 Nov;2008(31):5215-5220. doi: 10.1002/ejoc.200800704.
Abstract
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.
摘要
开发了一种7-氧杂降冰片烯的高度区域选择性多米诺复分解反应，该反应利用酰胺羰基与钌金属中心的分子内缔合。通过使用该反应，以12 - 14步高效合成了十二种受dysiherbaine启发的谷氨酸类似物；其中一种类似物表现出与中枢神经系统抑制一致的生物活性。
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本文引用的文献
1
The remarkable metal-catalysed olefin metathesis reaction.卓越的金属催化烯烃复分解反应。
Nature. 2007 Nov 8;450(7167):243-51. doi: 10.1038/nature06351.
2
Ring-rearrangement metathesis.环重排复分解反应
Chem Asian J. 2007 Sep 3;2(9):1064-82. doi: 10.1002/asia.200700072.
3
Ring-opening/ring-closing metathesis (RORCM) reactions of 7-Azanorbornene derivatives. An entry into perhydroindolines.7-氮杂降冰片烯衍生物的开环/闭环复分解（RORCM）反应。通往全氢吲哚啉的途径。
Org Lett. 2006 Feb 2;8(3):459-62. doi: 10.1021/ol052741g.
4
Metathesis reactions in total synthesis.全合成中的复分解反应。
Angew Chem Int Ed Engl. 2005 Jul 18;44(29):4490-527. doi: 10.1002/anie.200500369.
5
Total synthesis of salinosporamide A.沙利霉素A的全合成。
J Am Chem Soc. 2005 Jun 15;127(23):8298-9. doi: 10.1021/ja0522783.
6
Divergent pharmacological activity of novel marine-derived excitatory amino acids on glutamate receptors.新型海洋来源兴奋性氨基酸对谷氨酸受体的不同药理活性。
J Pharmacol Exp Ther. 2005 Sep;314(3):1068-78. doi: 10.1124/jpet.105.086389. Epub 2005 May 24.
7
Regioselective ring-opening/cross-metathesis reactions of norbornene derivatives with electron-rich olefins.降冰片烯衍生物与富电子烯烃的区域选择性开环/交叉复分解反应
Org Lett. 2005 Jan 6;7(1):131-3. doi: 10.1021/ol047808z.
8
Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton.（+）-真菌环氧二烯及相关天然产物（-）-1893A的不对称全合成：一锅法开环/交叉/关环复分解反应在构建其9-氧杂双环[4.2.1]壬-2,4-二烯骨架中的应用
J Org Chem. 2004 Dec 10;69(25):8789-95. doi: 10.1021/jo048566j.
9
Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis.通过闭环复分解反应合成含氮和氧的杂环化合物。
Chem Rev. 2004 May;104(5):2199-238. doi: 10.1021/cr0200872.
10
Highly regioselective ring-opening/cross-metathesis reactions of 2-sulfonylnorbornene derivatives.2-磺酰基降冰片烯衍生物的高度区域选择性开环/交叉复分解反应
Org Lett. 2004 May 13;6(10):1625-7. doi: 10.1021/ol049561b.
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