The strained bicyclo[4.2.0]oct-2,4-diene motif 1 has appeared in the literature contained within both molecules of physical organic interest and Australian-born natural products (e.g. Black et al. Aust.J. Chem. 1982, 35, 557-65; 567-79; 2247-56). Although there are a number of methods to synthesise this motif, most rely on the biomimetic approach. In search of an alternative method, chemists from The University of Queensland, led by Dr Craig Williams, have discovered that certain disubstituted cyclooctatetraenes will undergo cycloaddition with diazo compounds (e.g. DIAD) to give adducts of type 2, which, after partial hydrogenation, undergo cycloreversion to the target motif 1 (Grange R.L., Gallen M.J, Schill H., Johns J.P., Dong L., P.G., Reddell P.W., Gordon V.A., Bernhardt P.V., Williams C.M. Chem. Eur. J. 2010,16, 8894-903). In addition, the diazocycloadducts 2 were found to be active against certain cancer cell lines.
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