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Wilkie RP, Neal AR, Johnston CA, et al. Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi-Sakurai reaction. Chem Commun (Camb). 2016;52(71):10747-50doi: 10.1039/c6cc05747k.
Wilkie, R. P., Neal, A. R., Johnston, C. A., Voute, N., Lancefield, C. S., Stell, M. D., Medda, F., Makiyi, E. F., Turner, E. M., Stephen Ojo, O., Slawin, A. M., Lebl, T., Mullen, P., Harrison, D. J., Ireland, C. M., & Westwood, N. J. (2016). Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi-Sakurai reaction. Chemical communications (Cambridge, England), 52(71), 10747-50. https://doi.org/10.1039/c6cc05747k
Wilkie, Ross P, et al. "Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi-Sakurai reaction." Chemical communications (Cambridge, England) vol. 52,71 (2016): 10747-50. doi: https://doi.org/10.1039/c6cc05747k
Wilkie RP, Neal AR, Johnston CA, Voute N, Lancefield CS, Stell MD, Medda F, Makiyi EF, Turner EM, Stephen Ojo O, Slawin AM, Lebl T, Mullen P, Harrison DJ, Ireland CM, Westwood NJ. Total synthesis of dehaloperophoramidine using a highly diastereoselective Hosomi-Sakurai reaction. Chem Commun (Camb). 2016 Sep 14;52(71):10747-50. doi: 10.1039/c6cc05747k. Epub 2016 Aug 10. PMID: 27507662.
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Chem Commun (Camb). 2016 Sep 14;52(71):10747-50. doi: 10.1039/c6cc05747k. Epub 2016 Aug 10.

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

Chemical communications (Cambridge, England)

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

Affiliations

  1. School of Chemistry and Biomedical Sciences Research Complex, University of St. Andrews and EaStCHEM, St. Andrews, Fife, Scotland KY16 9ST, UK. [email protected].

PMID: 27507662 DOI: 10.1039/c6cc05747k

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.

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