title: A solid-phase, library synthesis of natural-product-like derivatives from an enantiomerically pure tetrahydroquinoline scaffold.
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)).
authors.affiliation: Chemical Biology Program, Steacie Institute for Molecular Sciences, National Research Council of Canada, 100 Sussex Drive, Ottawa, Ontario, Canada, K1A 0R6.
authors.forename: Samuel
authors.initials: S
authors.lastname: Couve-Bonnaire
authors.forename: Doug T H
authors.initials: DT
authors.lastname: Chou
authors.forename: Zhonghong
authors.initials: Z
authors.lastname: Gan
authors.forename: Prabhat
authors.initials: P
authors.lastname: Arya
mesh_terms: D001685:Biological Factors / Q000737:chemistry*; D002851:Chromatography, High Pressure Liquid; D020650:Combinatorial Chemistry Techniques; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011804:Quinolines / Q000737:chemistry*; D012997:Solvents; D013237:Stereoisomerism
chemical_list: D001685:Biological Factors; D007202:Indicators and Reagents; D011804:Quinolines; D012997:Solvents