Formation of some novel 9β-methyl-19-norpregnane derivatives

Abstract

The rearrangement of 9α,11α-epoxy-5α-pregnane-3β-20β-diyl diacetate (3) to 11-oxo-5α,9β-pregnane-3β,20β-diyl diacetate (4) and 11α-hydroxy-9β-methyl-19-norpregn-5(10)-ene-3β,20β-diyl diacetate (5) is reported. Treatment of the 5(10)-ene (5) with m-chloroperbenzoic acid in benzene affords 5β,10β-epoxy-11α-hydroxy-9β-methyl-19-norpregnane-3β,20β-diyl diacetate (11), whereas epoxidation with peracetic acid in acetic acid containing mineral acid (1% H₂SO₄) leads to 5α,11α-epoxy-10β-hydroxy-9β-methyl-19-norpregnane-3β,20β-diyl diacetate (12) by rearrangement of the initially formed 5β,10β-epoxide (11).