TARGET DRIVEN DEVELOPMENT OF METAL CATALYSED C–H B.. (CHACT)
TARGET DRIVEN DEVELOPMENT OF METAL CATALYSED C–H BOND ACTIVATION STRATEGIES FOR CHEMICAL SYNTHESIS OF ANTICANCER MOLECULES
Start date: 15 Feb 2008,
End date: 14 Oct 2009
"Chemical synthesis relies on the presence of functional groups to control the formation of new bonds. In many cases the presence of a particular functional group is of key importance to the target molecule, however frequently the motif is simply present to provide activation for the desired chemical step. The atom economy issues involved in these steps are problematic in two ways. Firstly, the group in question is not always in the final molecule and hence is wasted atomic material. Secondly, and more importantly, the installation of the functional moiety can involve multiple steps and thus reduce the efficiency of the synthesis. A central theme of the research in our group is development of a functional group free disconnection approach to chemical synthesis that uses metal catalysed C–H bond functionalisation to build molecules around simple starting materials.2 While we are not suggesting that this approach will replace the conventional tactics3 of molecule assembly it does offer the synthetic chemist the chance to explore completely unknown strategies. More specifically, it allows us to put the standard rulebook of disconnections to one side and invent a new set of reactions that allow us to break down a molecule without needing to locate a functional group in the synthons. Breaking a C–C, C–N or C–O bond back to a number of C–H bonds represents the pinnacle of modern synthetic chemistry. To achieve this would allow metal catalysed C–H bond functionalisation strategies to offer a conceptually new approach to synthesis that will compliment conventional synthesis and enable us to move a step closer to being able to assemble any desired molecule. • Target driven methodology development inspired synthesis of dictyodendrin B via a catalytic C–H bond activation strategy. • Development of iterative catalytic C–H bond activation tactics for the total functionalisation of heteroarenes. • Investigation of oxidative Pd(II) catalysed C–H bond amination strategies"
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