Synthesis of (3R)- and (3S)-Fluoro-(4R,5R)-dihydroxy-1-cyclohexene-1-carboxylic acids: The (3R)- and (3S)-fluoro analogues of (−)-shikimic acid

(3R)- and (3S)-Fluoro-(4R,5R)-dihydroxy-1-cyclohexene-1-carboxylic acids (the (3R)- and (3S)-fluoro analogues of (−)-shikimic acid) have been synthesised from (−)-shikimic acid via an intermediate epoxide (a fungal metabolite from Chalara microspora) that underwent acid catalysed hydrolysis to afford the first stereospecific synthesis of (−)-3-epi-shikimic acid.