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

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 installe...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (71), p.10747-10750
Main Authors: Wilkie, Ross P, Neal, Andrew R, Johnston, Craig A, Voute, Nicholas, Lancefield, Christopher S, Stell, Matthew D, Medda, Federico, Makiyi, Edward F, Turner, Emma M, Stephen Ojo, O, Slawin, Alexandra M Z, Lebl, Tomas, Mullen, Peter, Harrison, David J, Ireland, Chris M, Westwood, Nicholas J
Format: Article
Language:English
Subjects:
Biological activity
Cancer
Derivatives
Natural products
Stereochemistry
Synthesis
Synthesis (chemistry)
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Summary: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.
ISSN:1359-7345
1364-548X
DOI:10.1039/c6cc05747k