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Total synthesis of Histrionicotoxin

Robert Archer

31 Jan 2011

In December 2010 SCI awarded me a Messel travel bursary to attend the Pacifichem 2010 conference and present my work towards the total synthesis of Histrionicotoxin.

Pacifichem is a conference on a grand scale with over 10,000 delegates and more than 13,000 posters and oral presentations. The broad aim of the organisers is to promote scientific exchange for a sustainable future. To this end there were often more than forty talks occurring simultaneously covering a broad range of chemistry from Nanotechnology to Agrochemistry, Analytical Chemistry to Alternate Energy Technology. Even in my own area of Synthetic Organic Chemistry there were a wide variety of talks, which really suited me. I was able to listen to the latest research on areas I have been experimenting with during my PhD and also investigate other areas that could give me research ideas for the future.

I have quite a different background to most other PhD students. After studying Chemistry at the University of Durham I worked for five years as an Organic Chemist for Maybridge, a Synthetic Chemistry company specialising in the synthesis of heterocyclic molecules. At Maybridge I was able to work on custom synthesis projects, medicinal chemistry projects in collaboration with biotech companies and the synthesis of key library intermediates. The emphasis was always to synthesise high specification products in the shortest time possible, but the real joy for me was designing and then making new compounds using the organic chemistry theories I had learnt and researched.

After five years in that role I took the opportunity of studying for a PhD as part of the Bull group at the University of Bath. My PhD has focused on the synthesis of natural products containing 2-aza-spirocyclic cores and α-keto acids. I continue to be excited by the prospect of making new compounds, studying the latest chemical research to overcome problems encountered and adding to that research. My work has focused on the asymmetric aza-Michael reaction, enolate-imine condensation reactions and the use of natural and unnatural enzymes in organic synthesis. I was able to attend talks and see posters that focused on these areas at the conference: a wonderful opportunity to get some new ideas and to marvel at the achievements of some of the world leaders.

Some of the biggest names in organic synthesis were giving presentations, so it was brilliant to go and listen to people such as B List, K C Nicolaou, R H Grubbs, E N Jacobsen and D MacMillan. The manner of each one of these speakers differed greatly; from clear, concise and well-paced to broad, fast and perhaps even enigmatic. However, I walked away from each lecture very impressed by their delivery. Some would say that with large groups, famous researchers can easily churn out papers with impressive results. One thing that struck me about each of these scientists was their obvious fascination, passion and conviction. For no matter how clever the researcher or how big the group, surely, to be successful, scientists need real confidence and interest to pursue their research.

Some of the presentations I attended were from scientists such as final year PhD students and Post Doctoral workers. It was useful to see how they went about presenting their work especially because their presentations were not quite as well rounded or complete as those from experienced researchers. I learnt one valuable lesson in particular: if you show your data, ensure you fully understand it, know any potential inconsistencies and how these can be explained. One hapless chemist included some NMR data that he used to characterise intermediates involved in his reaction. The NMRs were visually very well presented and definitely improved his presentation, but during the question time he was shown up by one member of the audience, an expert on 13C NMR of the carbanions in question, who certainly didn’t agree with the conclusions reached.

I had the opportunity to present a poster on my progress towards the total synthesis of Histrionicotoxin, a natural product with a 2-aza-spirocyclic core. I hope the conversations I had during the poster session and the contacts I made will be of use in my career. I am certain that the lessons I have learnt at this conference and the inspiration I have gained will improve my thesis and my opportunities for the future. I would like to thank the SCI for the financial support they have given me, my supervisor and my industrial sponsor, Syngenta, for the opportunity to study for a PhD in Bath and attend the Pacifichem conference in beautiful Hawaii.

Robert Archer,
University of Bath

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