Synthesis of a broad array of highly functionalized, enantiomerically pure cyclohexanecarboxylic acid derivatives by microbial dihydroxylation of benzoic acid and subsequent oxidative and rearrangement reactions.
[reaction: see text]. 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 readily 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 substrate undergoes many specific oxidative and rearrangement processes. Among these are transformations of unanticipated chemical novelty and many products that have not been previously described.
Myers
A G
AG
Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138, USA. myers@chemistry.harvard.edu
Siegel
D R
DR
Buzard
D J
DJ
Charest
M G
MG
D019817:Benzoic Acid / Q000737:chemistry*; D003509:Cyclohexanecarboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D006900:Hydroxylation; D008968:Molecular Conformation; D010084:Oxidation-Reduction
D003509:Cyclohexanecarboxylic Acids; D019817:Benzoic Acid; C044895:cyclohexanecarboxylic acid