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  • Synthesis of two chiral octahydroindole scaffolds for drug discovery

    Author(s)
    Sydnes, Magne O
    Phuc, Van Le
    Olschimke, Jens
    Healy, Peter C
    Garavelas, Agatha
    Tajabadi, Fatemeh Mazraati
    Pedro, Liliana
    Quinn, Ronald J
    Jenkins, Ian D
    Griffith University Author(s)
    Jenkins, Ian D.
    Healy, Peter C.
    Quinn, Ronald J.
    Year published
    2016
    Metadata
    Show full item record
    Abstract
    There are over one thousand natural products that contain the octahydroindole scaffold, which can be considered a biologically validated starting point for the design of compound libraries. Two chiral octahydroindole scaffolds have been synthesized in multigram quantities in two steps from a readily available indoline. They contain either one or two amino groups (one Boc-protected) and a protected carboxylic acid group, and have been designed for ease of conversion to a lead generation library. The structures of both scaffolds have been established unequivocally by single crystal X-ray structure determination.There are over one thousand natural products that contain the octahydroindole scaffold, which can be considered a biologically validated starting point for the design of compound libraries. Two chiral octahydroindole scaffolds have been synthesized in multigram quantities in two steps from a readily available indoline. They contain either one or two amino groups (one Boc-protected) and a protected carboxylic acid group, and have been designed for ease of conversion to a lead generation library. The structures of both scaffolds have been established unequivocally by single crystal X-ray structure determination.
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    Journal Title
    Tetrahedron
    Volume
    72
    Issue
    9
    DOI
    https://doi.org/10.1016/j.tet.2016.01.018
    Subject
    Medicinal and biomolecular chemistry
    Organic chemistry
    Organic chemistry not elsewhere classified
    Publication URI
    http://hdl.handle.net/10072/142642
    Collection
    • Journal articles

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