Synthesis of a broad array of highly functionalized, enantiomerically purecyclohexanecarboxylic acid derivatives by microbial dihydroxylation of benzoic acid and subsequent oxidative and rearrangement reactions

[GRAPHICS] We have found that the 1,2-dihydroxylation of benzoic acid with Alcaligenes eutrophus strain B9, first reported in 1971 by Reiner and Hegeman, is read ily adapted for the preparation of tens to hundreds of grams of (1S,2R)-1,2 -dihydroxycyclohexa-3,5-diene-1-carboxylic acid of > 95% ee. This unique su bstrate undergoes many specific oxidative and rearrangement processes. Amon g these are transformations of unanticipated chemical novelty and many prod ucts that have not been previously described.