Difluorinated analogues of shikimic acid

Begum, L., Box, J.M., Drew, M.G.B., Harwood, L.M. ORCID: https://orcid.org/0000-0002-8442-7380, 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 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.