18 Nov 2015
Robert Foster was awarded a Messel travel bursary in 2015 for his attendance at the 250th American Chemical Society (ACS) National Meeting & Exposition, which was held in Boston, USA, between 16 and 20 August 2015. Below, he tells us how his participation in the conference gave him invaluable experience in presenting his work on endo-cantharimides to an international audience.
‘I would like to take this opportunity to sincerely thank SCI for awarding me with a Messel Travel Bursary of £850. With this I was able to attend the 250th American Chemical Society (ACS) National Meeting & Exposition, Boston, Massachusetts, USA, in August 2015. Attending this conference would not have been possible without the generous financial support of SCI.
‘The theme of the 250th ACS National Meeting & Exposition was ‘Innovation from discovery to application’, and the conference was notable for the quality of science on display. Perhaps my favourite presentation was given by Neil Garg on his group’s recent efforts of nickel-catalysed Suzuki-Miyaura cross-coupling of aryl carbamates and sulfamates with boronic acids. This powerful transformation was used to prepare a range of biaryl species from widely available phenol precursors. Another notable speaker was Richmond Sarpong, who gave an engaging presentation on strategies in total synthesis, including his recent work on the lycopdium alkaloids. Barry Trost gave a fascinating talk on palladium catalysed allylic substitutions which encompassed the length of his independent academic career, from early work on the Tsuji-Trost Reaction to recent developments in the field of enantioselective synthesis. Corey Stephenson provided an interesting update on his research in the area of single electron transfer processes and how it had been applied to trifluoromethylation reactions and the synthesis of complex alkaloid natural products. Dean Toste’s presentation was another highlight. He provided an insightful discussion on the application of chiral anions in enantioselective organic synthesis, including recent work on electrophilic fluorinations. It was also interesting to see many different speakers from different industrial backgrounds, including Anthony Wood’s discussion of the value of heterocyclic chemistry within Pfizer’s research output. I must also mention the many engaging presentations by postgraduate and postdoctoral researchers (both oral and poster) in organic and medicinal chemistry, which were a major part of my conference experience.
‘As part of attending the meeting I presented a poster entitled ‘Irreversible endo-selective Diels-Alder reactions of substituted alkoxyfurans: A general synthesis of endo-cantharimides’ at both the Heterocycles and Aromatics; New Reactions and Methodology and Sci-Mix poster sessions. I presented a paper of the same name published earlier this year in Chemistry: A European Journal (Chem. Eur. J. 2015, 21, 6107-6214) where we reported how 3-alkoxyfurans underwent the first known example of an irreversible furan-Diels-Alder reaction with different maleimides to access a novel class of hetereocycles that we named ‘endo-cantharimides’. By exploiting a Au(I)-catalysed synthesis of 3-alkoxyfurans we had developed previously in the Sheppard laboratory (Chem. Commun. 2014, 50, 1302-1304), we were able to access a selection of structurally diverse endo-cantharimides in an efficient, convergent and sustainable fashion. As part of the work we explored and discussed the potential application of endo-cantharimides within medicinal chemistry and investigated the unusual nature of the furan-Diels-Alder reaction with the aid of DFT calculations. Through presenting this poster at the ACS National Meeting I was able to discuss the work with researchers that had very different backgrounds and perspectives. Their feedback was positive and I had many valuable discussions as to how the work could be expanded. This included developing an asymmetric approach to endo-cantharimides, applying the chemistry to natural product synthesis and adapting the chemistry to access novel heterocyclic frameworks. A common point of discussion was our unusual choice of dimethyl carbonate (DMC) as solvent for the key cyclisation step. Many people were interested to hear how DMC has recently been promoted as a sustainable alternative to some traditional solvents (such as dichloromethane), as well as offering improved diastereoselectivity for our furan-Diels-Alder reaction. I also had several valuable discussion about the potential application of this chemistry in drug discovery and how we could pursue that in the future by expanding the methodology and with the aid of computational calculations.
‘Since attending the 250th ACS National Meeting & Exposition I have completed my PhD at University College London and have joined AstraZeneca as an industrial postdoctoral researcher. The two-year position will focus on the catalytic asymmetric access to quaternary amino acids, piperazenes, diketopierazenes and related systems, in collaboration with Professor Nigel Simpkins at the University of Birmingham. One thing I continuously had in mind while attending the meeting was how I could apply the ideas being presented to future research and this has had a direct impact on the work I have started to engage in. The meeting was also an excellent opportunity to meet new people from different scientific backgrounds, which I am sure will prove valuable in my future career.
‘I would like to thank SCI again for awarding a Messel Travel Bursary towards my attendance at 250th ACS National Meeting & Exposition in August 2015. The conference was an engaging, rewarding and enjoyable experience and one which will be greatly beneficial to my future career in research.’
Robert Foster
Postdoctoral Researcher, AstraZeneca
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