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 |
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| Authors: | Jane L Humphreys |
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| Institution: | School of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, UK |
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| 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). |
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| Keywords: | Shikimic acid Fluorination Antibacterial agents |
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