Exploring the Synthetic Applications of Enone Derived Amino Acids

The aim of this PhD programme will be to exploit enone derived amino acids for the preparation of a wide range of highly functionalised amino acids and peptides. Such compounds could find use in a wide range of applications including parasite selective fluorescent probes, new antibiotics of the diaminopimelic acid pathway and antitumour agents of glutamine biosynthesis. The PhD programme will also use enone derived amino acids as substrates for an efficient 6-endo-trig cyclisation to generate either anti- or syn-substituted 4-oxopipecolic acids. These synthetic intermediates will then be used for the synthesis of a range of piperidine-based natural products. Various aspects of the 6-endo-trig cyclisation will then be studied, such as trapping the resulting enolate with electrophiles allowing the generation of two stereogenic centres in a one-pot process. Further functionalisation of these compounds will be investigated for the preparation of highly substituted pipecolic acid derivatives and aza-sugars.