Properly protected derivatives 14 and 20 of the common precursor 17β-hydroxy-1-methyl-5α-androst-1-en-3-one ( 13) have been transformed in a regioselective manner into highly methylated androsta-1,4-diene-3,17-dione derivatives 6–8. Access to the manifold of 1,4-dimethylated derivatives was gained by methylation of the kinetic lithium dienolate derived from 20, while thiomethylation of 14, via the thermodynamic dienolate or an equivalent, followed by Raney nickel promoted desulfurization gave rise to 28. A combination of these alkylation methods led successfully to the trimethylated androstane derivative 34. Benzeneseleninic anhydride (BSA) mediated dehydrogenation of intermediates 23, 28, and 34 then furnished the 1,4-dienes 24, 29, and 35, two conventional steps short of the target molecules 6–8. A facile synthesis of the potent aromatase inhibitors 5 by subjecting 13 to a BSA-promoted oxidation is also described.