19th international isotope society (UK group) symposium: synthesis & applications of labelled compounds 2010

Allen, P.H, Bloom, A.J., Bragg, R., Brown, R.T., Burgos, A., Bushby, N., Clarke, M.L., Dudin, L.F., Ellames, G.L., Gee, A.D., Gouverneur, V., Harding, J.R., Harrowven, D.C., Herbert, J.M., Hickey, M.J., Husbands, S., Jennings, L.E., Jones, M., Kealey, S., Killick, D., Kingston, L.P., Kitson, S.L., Kohler, A., Kostiuk, S.L., Le Strat, F., Light, M.E., Lockley, W.J.S., Long, N.J., McNeill, A.H., Miller, P.W., Moody, T.S., Murrell, V.L., Nanson, L., Pedersen, M.H.F., Pinney, K.G., Plisson, C., Schou, S., Sharma, R.S., Shaw, I., Sherhod, R., Smith, T., Sriram, M., Tate, J., Tredwell, M., Twiddy, S., Watters, W., White, A.J.P., Wilkinson, D.J. and Woodcock, T. (2011) 19th international isotope society (UK group) symposium: synthesis & applications of labelled compounds 2010. Journal of Labelled Compounds and Radiopharmaceuticals, 54 (7), 387-398. (doi:10.1002/(ISSN)1099-1344).

Abstract

The 19th annual symposium of the International Isotope Society’s United Kingdom Group took place at the Wellcome Genome Campus, Hinxton, Cambridge, UK on Thursday 14th October 2010. The meeting was attended by around 80 delegates from academia and industry, the life sciences, chemical, radiochemical and scientific instrument suppliers.

The Harrowven contribution:
Since Kekule ? first proposed his ouroboros-inspired structure for benzene in the mid-nineteenth century, it has been regarded as the archetypal aromatic compound – flat, with carbon-carbon bonds of equal length and bond angle.1 The viability of non-planar benzene rings has been known for many decades, with the first reported example of a boat-configured arene dating to the synthesis of [2.2]paracyclophane in 1949.2 However, it was arguably the isolation of (1)-cavicularin in 1996, and latterly of the haouamines and hirsutellones, that alerted the wider scientific community to the existence of biosynthetic pathways for the generation of such motifs in Nature (Figure 1).

Through a combination of chemical synthesis (cavicularin,3,4 riccardin C3,4 and RP-664534), molecular modelling and data mining, we have strong evidence to suggest that boat-configured arenes are far more common in natural products than has been traditionally thought, spanning many classes including macrocyclic alkaloids, guaianolides, bisbibenzyls, peptides and biarylheptanoids. In addition, our work provides guidance for addressing the chemical synthesis of such targets.

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Contributors

Author: D.C. Harrowven

Author: M.E. Light

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