Microbial Stereodifferentiating Reduction of 2,6-Adamantanedione and Hexahydrodibenzoheptalene-5,11-dione, Diketones with Two Homotopic Carbonyl Groups on a C2 Symmetry Axis

Article abstract of DOI:10.1021/jo00319a022

The microbial stereodifferentiating aptitude toward diketones with two homotopic carbonyl groups on a C₂ symmetry axis was studied.Incubating of 2,6-adamantanedione (6) with Curvularia lunata yielded, via the ketol 10, (-)-(R)-2,6-adamantanediol (11), and incubation with Rhodotorula rubra converted the (+/-) doubly bridged biphenyl diketone 7 into a mixture of the recovered (+)-(R)-diketone 7, the (+)-(R)-ketol, and the (-)-(S)-cis-diol 19.These stereoselectivities were analyzed to test the proposed "C₂-ketone rule".