Transformation of 3-oxo-17-ethylenedioxy-19-mesyloxy-delta-1,4-androstadiene in 3 instances to A-homo-19-norsteroids

4-oximino-17-ethylenedioxy-A-homo-δ^1(10),2,4a-19-nor-androstatriene is formed by treatment of 3-oximino-17-ethylenedioxy-19-mesyloxy-δ^1,4-androstadiene with sodium hydroxide. An analogous reaction occurs with the corresponding semicarbazone, but under the same conditions 3-hydrazino-17-ethylenedioxy-19-mesyloxy-δ^1,4-androstadiene leads to 17-ethylenedioxy-A-homo-δ^2,4,5(10)-19-norandrostatriene.