Organic synthesis

Dr Joanne Harvey and Associate Professor Paul Teesdale-Spittle

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.

Amira Brackovic works on the synthesis of bioactive natural product peloruside A
Amira Brackovic works on the synthesis of bioactive natural product peloruside A.

Our research is based in the Schools of Chemical and Physical Sciences and Biological Sciences at Victoria University of Wellington and forms part of the activities of the Centre for Biodiscovery. Our lab space is located in the purpose-built Alan MacDiarmid building and we benefit from extensive NMR facilities within the School.

Chemical compounds synthesised by the Organic Synthesis group
A selection of the compounds being synthesised by our group.

Chemical synthesis and the extraction of natural products from plants, algae and bacteria are complementary methods for discovering novel and bioactive molecules. Natural compounds produced by the organism for defence or other biological processes often have interesting bioactivity based on the structure of the compounds. Although these compounds can be highly active, often the harvesting of sufficient quantities for pharmaceutical or other applications is ecologically unsound, due to the small amounts that are naturally present.

Synthetic organic chemistry however, enables us to generate equivalent compounds on a useful scale. We can also make many rationally designed chemical analogues, based on the natural bioactive compound, which may have enhanced activity for a particular purpose.

Together, these two complementary methods provide a pipeline for the discovery and development of bioactive compounds for therapeutic use.

Following on from our total synthesis of the macrocyclic resorcylic acid lactone (RAL), aigialomycin D (see J. Org. Chem. 2009, 74, 2271), we are synthesising several analogues in order to investigate the relationships between structure and function in the RAL molecules.

The group is also working on synthesising the following natural products and/or their analogues:

  • zampanolide
  • peloruside A
  • pateamine
  • labillarides E-H
  • lehualides E-K
  • TAN-2483B.

Methods for synthesising modified sugars, such as C-glycosides, C-branched carbohydrates and oxepines have been developed (see Chem. Commun. 2011, J. Org. Chem. 2010) and are being further studied.

See publications for further information

See people for contact information.

Read more about our research projects.