ISOMERIZATION OF 14-HYDROXY-17-KETOSTEROIDS: NEW EXAMPLES OF TWO-CENTERED INVERSION OF THE C/D RING FUSION AND X-RAY DIFFRACTION STRUCTURAL ANALYSIS OF d,l-3-METHOXY-14β-HYDROXY-8β,9α-ESTRA-1,3,5(10)-TRIEN-17-ONE

Article abstract of DOI:10.1007/BF00959735

d,l-3-Methoxy-14β-hydroxy-8α,9β-estra-1,3,5(10)-trien-17-one (I) undergoes two-centered isomerization in alkaline medium to d,l-3-methoxy-14β-hydroxy-8β,9α-estra-1,3,5(10)-trien-17-one (II) in 70percent yield.Under unalogous conditions, natural isomer (II) is converted into synthetic isomer (I) in 20percent yield.The crystalline and molecular structure of isomer (II) was established.