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基于四氢喹啉的多环衍生物的立体选择性多样性导向溶液和固相合成

Stereoselective diversity-oriented solution and solid-phase synthesis of tetrahydroquinoline-based polycyclic derivatives.

作者信息

Arya Prabhat, Durieux Patricia, Chen Zai-Xin, Joseph Reni, Leek Donald M

机构信息

Chemical Biology Program, Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, Canada, K1A 0R6.

出版信息

J Comb Chem. 2004 Jan-Feb;6(1):54-64. doi: 10.1021/cc034053z.

DOI:10.1021/cc034053z
PMID:14714985
Abstract

A diversity-oriented solution and solid-phase synthesis of tetrahydroquinoline-based tricyclic derivatives has been achieved from enantiomerically pure, natural product-like bicyclic scaffold. The solution synthesis of enantiopure bicyclic scaffold was developed by asymmetric hetero Michael reaction. Our approach for the synthesis of polycyclic derivatives utilized regio- and stereoselective hetero Michael reaction and ring-closing metathesis as key steps in solution and on solid phase.

摘要

从对映体纯的、类似天然产物的双环骨架出发,实现了基于四氢喹啉的三环衍生物的多样性导向合成及固相合成。对映体纯双环骨架的溶液合成是通过不对称杂迈克尔反应开发的。我们合成多环衍生物的方法利用区域和立体选择性杂迈克尔反应以及闭环复分解反应作为溶液和固相中的关键步骤。

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Stereoselective diversity-oriented solution and solid-phase synthesis of tetrahydroquinoline-based polycyclic derivatives.基于四氢喹啉的多环衍生物的立体选择性多样性导向溶液和固相合成
J Comb Chem. 2004 Jan-Feb;6(1):54-64. doi: 10.1021/cc034053z.
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Part 3. a novel stereocontrolled, in situ, solution- and solid-phase, Aza Michael approach for high-throughput generation of tetrahydroaminoquinoline-derived natural-product-like architectures.第3部分。一种新颖的立体控制、原位、溶液和固相氮杂迈克尔方法,用于高通量生成四氢氨基喹啉衍生的类天然产物结构。
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引用本文的文献

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Tetrahydroquinoline-derived macrocyclic toolbox: the discovery of antiangiogenesis agents in zebrafish assay.四氢喹啉衍生的大环工具库:斑马鱼实验中抗血管生成剂的发现
ACS Med Chem Lett. 2013 May 24;4(7):666-70. doi: 10.1021/ml400026n. eCollection 2013 Jul 11.
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Efficient synthesis and free-radical scavenging capacity of new 2,4-substituted tetrahydroquinolines prepared via BiCl₃-catalyzed three-component Povarov reaction, using N-vinylamides.高效合成及自由基清除能力的新 2,4-取代四氢喹啉通过 BiCl3 催化的三组分 Povarov 反应,使用 N-乙烯基酰胺。
Mol Divers. 2011 Nov;15(4):1007-16. doi: 10.1007/s11030-011-9330-5. Epub 2011 Sep 25.