New methodology for the stereoselective synthesis of unnatural alpha-amino acids

Drummond, Lorna J. (2011) New methodology for the stereoselective synthesis of unnatural alpha-amino acids. PhD thesis, University of Glasgow.

Abstract

New general methodology for the stereoselective synthesis of unnatural alpha-amino acids has been developed. Early work focussed on investigating methods for the generation of chiral allylic alcohols using cross-metathesis of a simple enone with various terminal alkenes, followed by an asymmetric ketone reduction.

The allylic alcohols were then converted to protected allylic amines via Overman rearrangement chemistry. Oxidative alkene cleavage and hydrolysis of these intermediates generated a range of alpha-amino acid targets. Attempts were also made to apply the developed methodology to the synthesis of a simple alpha,alpha-disubstituted alpha-amino acid target.

The Overman rearrangement was also applied to the generation of a late-stage intermediate which could be used in the synthesis of (2S,3S)-capreomycidine, a component of a number of peptides which exhibit antibacterial activity.

• Item Type: Thesis (PhD)
• Qualification Level: Doctoral
• Keywords: amino acids, organic synthesis
• Subjects: Q Science > QD Chemistry
• Colleges/Schools: College of Science and Engineering > School of Chemistry
• Supervisor's Name: Sutherland, Dr. Andrew
• Date of Award: 2011
• Depositing User: Miss Lorna Drummond
• Unique ID: glathesis:2011-2827
• Copyright: Copyright of this thesis is held by the author.
• Date Deposited: 05 Oct 2011
• Last Modified: 10 Dec 2012 14:00
• URI: https://theses.gla.ac.uk/id/eprint/2827