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Mingwu Ding - One of the best experts on this subject based on the ideXlab platform.

Alexandre V. Ivachtchenko - One of the best experts on this subject based on the ideXlab platform.

Laura West - One of the best experts on this subject based on the ideXlab platform.

David E. Portlock - One of the best experts on this subject based on the ideXlab platform.

Christopher Hulme - One of the best experts on this subject based on the ideXlab platform.

  • Expeditious Routes to Polycyclic Molecular Frameworks via One-Pot, Two-Step Ugi Ring-Closing Sequences
    Synlett, 2013
    Co-Authors: Fabio De Moliner, Alexandra P. Cappelli, Muhammad Ayaz, Christopher Hulme
    Abstract:

    A very general and robust multicomponent-reaction protocol involving an Ugi Condensation between ethyl glyoxylate, isonitriles, N -Boc-α-amino acids, and mono - N -Boc-protected diamines followed by a series of acid-promoted cyclization steps in a one-pot fashion is reported. This process allows for the assembly of complex polycyclic structures by means of just two simple synthetic operations and a single chromatographic purification in high overall yields. Of note, the first scaffolds derived from a highly ­selective sequence of ring-closing events involving three internal amino nucleophiles is reported.

  • MCC/SNAr methodology. Part 2: Novel three-step solution phase access to libraries of benzodiazepines
    Tetrahedron Letters, 2003
    Co-Authors: Paul Tempest, Liping H. Pettus, Vijay Keshav Gore, Christopher Hulme
    Abstract:

    Abstract New developments in the search for novel pharmacological agents over the last decade have focused on the preparation of chemical libraries as sources for new leads for drug discovery. To aid this search a plethora of personal synthesizers and new automation technologies have emerged to help fuel the lead discovery engines of drug discovery organizations. In fact, multi-step solid-phase syntheses of diverse libraries in excess of 10,000 products are now feasible via split and mix techniques. At the same time, a multitude of more efficient, diversity or target oriented solution phase chemical methodologies have appeared in the chemical literature, which have enabled the relatively facile construction of successful lead generation libraries with low FTE input and little capital expenditure. This communication reveals a further application of N -BOC-α-aminoaldehydes in the Ugi Condensation reaction, followed by a secondary S N Ar cyclization, accessing arrays of biologically relevant benzodiazepines in good yield and overall purity.