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Issue 71, 2016
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Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi–Sakurai reaction

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Abstract

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.

Graphical abstract: Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi–Sakurai reaction

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Publication details

The article was received on 13 Jul 2016, accepted on 05 Aug 2016 and first published on 05 Aug 2016


Article type: Communication
DOI: 10.1039/C6CC05747K
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Citation: Chem. Commun., 2016,52, 10747-10750
  • Open access: Creative Commons BY license
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    Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi–Sakurai reaction

    Ross. P. Wilkie, A. R. Neal, C. A. Johnston, N. Voute, C. S. Lancefield, M. D. Stell, F. Medda, E. F. Makiyi, E. M. Turner, O. Stephen Ojo, A. M. Z. Slawin, T. Lebl, P. Mullen, D. J. Harrison, C. M. Ireland and N. J. Westwood, Chem. Commun., 2016, 52, 10747
    DOI: 10.1039/C6CC05747K

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