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A Solid-Phase, Library Synthesis of Natural-Product-Like Derivatives from an Enantiomerically Pure Tetrahydroquinoline Scaffold

Samuel Couve-Bonnaire 1 Doug Chou 1 Zhonghong Gan 1 Prabhat Arya 1 
1 CNRC - Conseil National de Recherches Canada
Abstract : With the goal of developing a library synthesis of tetrahydroquinoline-derived natural-product-like small molecules, a practical synthesis of enantiomerically pure tetrahydroquinoline scaffold was achieved. An asymmetric aminohydroxylation reaction was the key step in this strategy. This scaffold was further immobilized onto the solid support for the library generation. The library was obtained from three diversity sites: (i) acylation of the hydroxyl group (R(1)), (ii) coupling of the Fmoc-protected amino acid to the amino group (R(2)), and (iii) amidation of the N-terminal amine group (R(3)).
Keywords : Biological Factors/chemistry* Chromatography High Pressure Liquid Combinatorial Chemistry Techniques Indicators and Reagents Magnetic Resonance Spectroscopy Quinolines/chemistry* Solvents Stereoisomerism
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https://hal-normandie-univ.archives-ouvertes.fr/hal-02384490
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Submitted on : Thursday, November 28, 2019 - 1:51:15 PM
Last modification on : Wednesday, April 15, 2020 - 11:26:02 AM

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Samuel Couve-Bonnaire, Doug Chou, Zhonghong Gan, Prabhat Arya. A Solid-Phase, Library Synthesis of Natural-Product-Like Derivatives from an Enantiomerically Pure Tetrahydroquinoline Scaffold. Journal of Combinatorial Chemistry, 2004, 6 (1), pp.73-77. ⟨10.1021/cc030026x⟩. ⟨hal-02384490⟩

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