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Title: Asymmetric lactam synthesis
Author: Harris, Matthew Eben
Awarding Body: University of Warwick
Current Institution: University of Warwick
Date of Award: 2013
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Broad-Spectrum Chemokine Inhibitors (BSCIs) are a novel type of antiinflammatory drug, discovered by Fox and colleagues. We have shown that the syntheses of C-substituted γ-thialactams are possible via a modular approach starting from the simple amino acid cystine. These compounds are a new class of GPCR ligand, showing BSCI activity comparable to their non-sulfur counterparts. Initial migratory data suggests that these lactams are inhibitors of leukocyte migration and comparable to the analogous BSCI lactams at μM concentrations, with decreased activity at the nM scale. Efforts have been made to the synthesis of substituted piperidinones, as well as employing Jocic-Reeve-Corey-Link chemistry to the general synthesis of lactams, ultimately looking to the synthesis of C-substituted lactams. Attempting to utilise trichloromethyl carbinol chemistry for these purposes has led to the synthesis of stereochemically-pure heterocycles containing up to 3 stereocentres. α- Trichloromethyl carbinols and asymmetric transfer hydrogenation chemistry are used from simple starting materials. Developments of this type of chemistry will undoubtedly lay the foundations to produce further non-racemic substituted heterocycles which will be important both synthetically and biologically.
Supervisor: Not available Sponsor: Engineering and Physical Sciences Research Council (EPSRC)
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry