Synthesis of optically active derivatives of bicyclic chiral diols with C₂ symmetry

Efficient synthesis, besides other, of dibromide, diazide, diamine and diesters derived from (11R,12R)-9,10-dihydro-9,10-ethanoanthracene-11,12-dimethanol (3), a chiral bicyclic diol with C 2 symmetry, was developed. Esterification of 3 with saturated and unsaturated carboxylic acids and acids chlorides leads to the corresponding normal-, olefinic- and acetylenic diesters in average yields of 81%. Also more efficient techniques for the preparation of starting diol 3 in higher yields as well as for a very simple separation of DCU from reactions carried out following DCC/DMAP method are described.