Difluorinated analogues of shikimic acid

Abstract 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)2Ph]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.