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Difluorinated analogues of shikimic acid

Begum, L., Box, J.M., Drew, M.G.B., Harwood, L.M., Humphreys, J.L., Lowes, D.J., Morris, G.A., Redon, P.M., Walker, F.M. and Whitehead, R.C. (2003) Difluorinated analogues of shikimic acid. Tetrahedron, 59 (26). pp. 4827-4841. ISSN 0040-4020

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To link to this article DOI: 10.1016/S0040-4020(03)00697-5

Abstract/Summary

Investigations into the quinate to shikimate transformation have been carried out, the results of which have been exploited in the synthesis of a novel difluoromethylene homologue of shikimic acid from (-)-quinic acid. Martin's sulfurane {Ph2S[OC(CF3)(2)Ph](2)} was the reagent of choice for the key dehydration step of this synthesis. The results of investigations into the synthesis of the important natural product analogue, 6,6-difluoroshikimic acid are also reported. (C) 2003 Elsevier Science Ltd. All rights reserved.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11017
Uncontrolled Keywords:shikimic acid, Martin's sulfurane, fluorinated analogues , APICOMPLEXAN PARASITES, (-)-SHIKIMIC ACID, PATHWAY, EFFICIENT, REAGENTS, MONOALKYLATION, DERIVATIVES, PROTECTION, FLUORIDE, DIOLS

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