Arene cis-dihydrodiols—useful precursors for the preparation of antimetabolites of the shikimic acid pathway: application to the synthesis of 6,6-difluoroshikimic acid and (6S)-6-fluoroshikimic acid

Abstract: The synthesis of 6,6-difluoroshikimic acid ( 11 ) has been achieved in ten steps from the enantiopure diol 16 , which is derived from enzymatic cis-dihydroxylation of iodobenzene. The versatility of the synthetic strategy has been demonstrated by the preparation of the known antimicrobial agent, (6S)-6-fluoroshikimic acid ( 5 ). [Copyright &y& Elsevier]