Synthesis of 5,10-seco analogs of testosterone

A number of 5,10-seco analogs of testosterone has been synthesized starting from products of the radical oxidation of 3β,17β-diacetoxy-5α-androstan-5α-ol. The obtained compounds possess a flexible 10-membered ring with substituents (O, –OH) at C-3 and C-5. Similar derivatives with an (E)- and (Z)-Δ1(10)-double bond have been prepared also. X-ray analysis and a combination of NMR experiments have been used for their structure elucidation and conformation analysis.