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Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi-Sakurai reaction.

Ross P Wilkie, Andrew R Neal, Craig A Johnston, Nicholas Voute, Christopher S Lancefield, Matthew D Stell, Federico Medda, Edward F Makiyi, Emma M Turner, O Stephen Ojo, Alexandra M Z Slawin, Tomas Lebl, Peter Mullen, David J Harrison, Chris M Ireland, Nicholas J Westwood
Chemical Communications : Chem Comm 2016 September 15
The synthesis of dehaloperophoramidine, a non-halogenated derivative of the marine natural product perophoramidine, and its biological activity towards HCT116, HT29 and LoVo colorectal carcinoma cells is reported. A [3,3]-Claisen rearrangement and an epoxide opening/allylsilylation reaction installed the contiguous all-carbon quaternary stereocentres with the required relative stereochemistry.

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