PhD (General)

My work covers two main areas:

The first is to continue the development of a new synthetic methodology for the synthesis of polyhydroxylated and alkylated indolizidines. The nucleophilicity of pyrrole is going to be used to achieve this through the synthesis of γ-pyrrolic esters which will then undergo acylation with the nucleophilic 2-position of the pyrrole ring.

This will synthesise the bicyclic indolizidine skeleton (advanced intermediate), which will be chemically modified to introduce substituents such that the substituted indolizidines will be synthesised.

Based on initial work, a second approach will also be employed to modify the simple pyrrole before formation of the “advanced intermediate” to allow access to more difficult targets, for example tri-substituted nuclei. Development of this proposed approach should allow synthesis of indolizidines in greater yield with less chemical manipulation than previous methods.

The second is synthesis of class of Phytotoxins called Thaxtomins, which are produced by the soil bacterium Streptomyces scabies. This synthesis will be a Biomimetic approach, starting from the natural amino acid tryptophan. Resulting compounds will be used for Bioassay testing in conjunction with the Tasmanian Institute for Agricultural Research.