A practical method for the synthesis of homochiral 2,10 camphanediols

Article abstract of DOI:10.1055/s-1991-26617

The esters 3a and 3b are conveniently prepared from (+)-ketopinic acid (7,7-dimethyl-2-oxobicyclo[2.2.1]heptane-1-carboxylate, 1) and are subsequently reduced to afford exo- and endo-2,10-camphanediols [1-(hydroxymethyl)-7,7-dimethylbicyclo [2.2.1]heptan-2-ols, 4a and 4b, respectively] in good overall yield. The alkylation of ester 3a with buyllithium gives only exo-10,10-dibutyl-2,10-camphanediol [exo-1-(1-butyl-1-hydroxypentyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-ol, 5] in good yield.