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

Abstract

(3 R)- and (3 S)-Fluoro-(4 R,5 R)-dihydroxy-1-cyclohexene-1-carboxylic acids (the (3 R)- and (3 S)-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.