Synthesis of (+)- and (–)-methyl shikimate from benzene

Abstract

cis-Cyclohexa-3,5-diene-1,2-diol 2, the product of oxidation of benzene by mutants of Pseudomonas putida, was transformed into optically pure 4 in a sequence involving asymmetrization of meso-diol 3 in organic media with Pseudomonas cepacia lipase. Alcohol 4 was converted into the title compounds by processes utilizing α-iodination of the derived enones 8 and 9 followed by Pd⁰-catalysed coupling of the α-iodoenones with 2-tributylstannylfuran and RuO₄-catalysed oxidation of the 2-furyl groups to carboxylic acids.