OXIDATIVE β-FRAGMENTATION OF 19-NOR-5α-ANDROSTANE-3β,5,17β-TRIOL 3,17-DIACETATE

Article abstract of DOI:10.1016/S0040-4020(01)88672-5

The preparation of 19-nor-5α-androstane-3β,5,17β-triol 3,17-diacetate (10) is described.When this alcohol was treated with the mercuric oxide-iodine reagent, it underwent fragmentation of the C(5)-C(10) bond with formation of a new type of 10-membered ring containing 5,10-seco-steroidal compounds, i.e. (Z)-and (E)-19-nor-3β,17β-diacetoxy-5,10-seco-androst-1(10)-en-5-one (11 and 12), in 27 and 49percent yield, respectively.