Organic Synthesis

Organic Synthesis

Description

We synthesise natural products and their structural analogues, applying new methodology we develop. Our synthetic targets are bioactive macrocyclic natural products and their analogues, and those that can be made through reactions of cyclopropanes.

Expertise

We synthesise natural products and their structural analogues. Our synthetic targets are bioactive macrocyclic natural products and their analogues, and those that can be made through reactions of cyclopropanes. Our research is based in the Schools of Chemical and Physical Sciences and Biological Sciences at Victoria University and forms part of the activities of the Centre for Biodiscovery. We have recently moved into new lab space in the purpose–built Alan MacDiarmid building and benefit from extensive NMR facilities within the School.

Objective

This group aims to discover novel bioactive molecules for therapeutic use through synthetic organic chemistry.

Research Focus

Total Synthesis of Natural Products

We are working on the synthesis of a family of New Zealand marine natural products, the labillarides. These molecules were discovered by Peter Northcote’s group at Victoria University and have unique structures. Their synthesis requires the development of new methodology and will confirm the structures assigned to these natural products, allow their stereochemistry to be determined and enable us to study their bioactivities in full.

Synthesis of Natural Product Analogues

We are working towards the syntheses of several simplified analogues of the New Zealand natural product peloruside A, a microtubule targeting agent discovered by the Northcote group at Victoria University. Our objective is to design an active analogue that can be easily synthesised with methods suitable for industrial scale–up. This would solve the current supply problems encountered with peloruside A and could enable a peloruside–type molecule to enter the market.

Synthesis of New Designed Compounds

We have discovered that sugar molecules with an attached cyclopropane ring partake in ring opening reactions to give various products depending on the reaction conditions. We are investigating the mechanism by which these processes occur and the scope of the resultant products.

Development of Synthetic Methodology

We are investigating an interesting side reaction in the well–known Horner–Wadsworth–Emmons reaction. The side reaction decreases the yield of the desired product but may be useful for producing alkene–phosphonates. We are currently fine–tuning the reaction conditions and learning how to control one pattern of reactivity over the other.