Moss, Sam (2014) New Synthetic Methods to Access Non-Coded Amino Acids. Doctoral thesis, University of Huddersfield.

-Amino acids are a ubiquitous class of compounds which are vital to the existence of all life on earth. In addition to providing the building blocks of life’s machinery, they are increasingly finding use as starting materials for total syntheses, as ligands in chiral catalysis or as novel pharmaceutically active compounds in their own right. As such, the development of new synthetic methods to access existing -amino acids, as well as previously unknown amino acids is of significant importance.
The introduction contained in the first part of this report aims to provide a general overview of the catalytic methods currently used to prepare -amino acids, as well as to highlight a notable class of -amino acids called the kainoids, with specific attention directed to covering previous total synthesis routes to access (-)--kainic acid.
The work described in the second part of this report was based on the extension of methodology developed by Shaw, and focuses on attempts to develop catalytic, diastereoselective aldol reaction methodology with azido hydroxamic acid-containing substrates in order to prepare diastereomerically pure -amino acids.
The third and final section of this report discusses the preparation of substituted tetrahydropyridinium ylide precursors and their subsequent rearrangement in the presence of neutrally-generated benzyne is explored. The selectivity observed when asymmetric arynes are generated as reactive species was also investigated. Finally, the successful expansion of this methodology to acyclic substrates is also discussed.

Thesis_Corrected_FINAL_DRAFT - Moss.pdf - Submitted Version

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