The compound 17β,19-dihydroxyandrost-4-en-3-one is similarly etherified to form the 17β-OR4, 19-OR1, derivatives of androst-4-en-3-one. Reduction as previously described yields the corresponding 3-hydroxy analogues. For example, 17β,19-dihydroxyandrost-4-en-3-one is converted to 17β,19-di-triphenylsiloxyandrost-4-en-3-one and 17β,19-di-(1-methoxy-1-cyclopentyloxy)-androst-4-en-3-one as previously described. These compounds are then reduced using lithium aluminum hydride in an ether or tetrahydrofuran solution to produce 17β,19-di-triphenylsiloxyandrost-4-en-3β-ol and 17β,19-di-(1-methoxy-1-cyclopentyloxy)-androst-4-en-3β-ol, respectively.
