SYNTHESIS OF OPTICALLY-ACTIVE ENDO,ENDO BICYCLO[2.2.2]OCTANE-2,5-DIOL, BICYCLO[2.2.2]OCTANE-2,5-DIONE, AND RELATED-COMPOUNDS

Optically active C-2-symmetric (1S,2S,4S,5S)-bicyclo[2.2.2]octane-2,5- diol ((+)-12; 98% ee) and several selectivity protected optically acti ve intermediates useful for synthetic transformations were synthesized via a 1,2-carbonyl transposition route starting from the easily avail able optically active (1R,4S,6S)-6-hydroxybicyclo[2.2.2]octan-2-one (( -)-2). The synthetic route also allowed the preparation of optically a ctive (1S,4S)-bicyclo[2.2.2]octane-2,5-dione ((+)-14; 98% ee).