Absolute stereochemistry of the dihydroanthracene-cis- and trans-1,2-diols produced from anthracene by mammals and bacteria

Abstract

(+)-1,2-Dihydroanthracene-trans- and -cis-1,2-diols have been isolated as major anthracene metabolites from rabbits and the bacterium Beijerinckia B-836, respectively. The absolute stereochemistry and optical purity of each diol has been related to that of 1,2,3,4-tetrahydroanthracen-2-ol. The latter was resolved via the diastereoisomeric (–)-methyloxyacetates, whose optical purity and absolute stereochemistry was determined by a range of techniques including kinetic resolution, asymmetric synthesis, and c.d. (exciton chirality method).