Two syntheses of the bicyclic α-ketols, 8a-hydroxy-4a-methyl-trans- and -cis-octahydronaphthalen-1(2H)-ones (1and2), have been effected. One involves epoxidation of 4a-methyl-1,2,3,4,4a,5,6,7-octahydronaphthalene (4), followed by hydrolysis and oxidation; direct "hydroxy ketonization" of4was found not to be practicable. The second involves treatment of 3,4,5,6,7,8-hexahydronaphthalen-1(2H)-one (14) with lithium dimethylcuprate, trimethylsilylation of the resulting enolate, oxidation of the enol ether, and hydrolysis. Syntheses of the 2α-deutero derivatives of1and2are also described.