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Asymmetric lactam synthesis
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Harris, Matthew Eben (2013) Asymmetric lactam synthesis. PhD thesis, University of Warwick.
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WRAP_THESIS_Harris_2013.pdf - Submitted Version Download (6Mb) | Preview |
Official URL: http://webcat.warwick.ac.uk/record=b2692894~S1
Abstract
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.
Item Type: | Thesis (PhD) |
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Subjects: | Q Science > QD Chemistry |
Library of Congress Subject Headings (LCSH): | Asymmetric synthesis, Lactams -- Synthesis, Anti-inflammatory agents, Chemical inhibitors |
Official Date: | May 2013 |
Institution: | University of Warwick |
Theses Department: | Department of Chemistry |
Thesis Type: | PhD |
Publication Status: | Unpublished |
Supervisor(s)/Advisor: | Fox, D. J. (David J.) |
Sponsors: | Engineering and Physical Sciences Research Council (EPSRC) |
Extent: | xxiii, 254 leaves : illustrations. |
Language: | eng |
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