Difluorinated analogues of shikimic acid

TitleDifluorinated analogues of shikimic acid
Publication TypeJournal Article
Year of Publication2003
AuthorsBegum, L, Box JM, Drew MGB, Harwood LM, Humphreys JL, Lowes DJ, Morris GA, Redon PM, Walker FM, Whitehead RC
ISBN Number0040-4020
Accession NumberWOS:000183780900016

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.