Preparations of Some Steroidal Diosphenols

Some 4, 4-dimethy1-2-hydroxy-Δ1-3-one type steroids (diosphenols) were prepared as potential tumor growth inhibiting chemotherapeuticals modeled on the cancer inhibiting elatericin B. These substances were obtained from 4, 4-dimethyl-3-oxo steroids by selenium dioxide oxidation, by a method via the 2-bromo compound, by a method via the 2-oximino compound or by autooxidation. The last two procedures were found to be the most suitable for the preparation of the desired substances.The diosphenols we obtained were as follows: 2-hydroxylanosta-1, 8, 24-trien-3-one (VIa), 2-hydroxylanosta-1, 8-dien-3-one (VIb), 2-hydroxy-3-oxo-4, 4, 14α-trimethyl-Δ1, 8-5α-choladienicacid (VId), 2, 17β-dihydroxy-4, 4-dimethylandrosta-1, 5-dien-3-one (XVIa), 2-hydroxy-4, 4-dimethyl-22α-spirosta-1, 5-diene-3-one (XVIc), 3-oxo-2, 12α-dihydroxy-4, 4-dimethyl-Δ1, 5-choladienic acid (XXIa), 2-hydroxy-3, 12-dioxo-4, 4-dimethyl-Δ1, 5-choladienic acid (XXVa), and 2-hydroxy-4, 4-dimethylergosta-1, 5, 7, 22-tetraen-3-one (XXVIII). 4-Hydroxy-3, 12-dioxo-Δ4-cholenic acid (XXVII) was also prepared.