The Reaction of Lead Tetraacetate with Progesterone and Testosterone

Preparation of Perhydronaphthalene-1,8-dione from 1,4,4aβ,5,8,8aβ-Hexahydronaphthalen-5α-ol-1,4-dione Acetate

“…Found for C12H1604: C, 64.34; H, 7.27. The tetrahydro compound (3), m.p. 95-96°, could also be obtained in lower yield by catalytic hydrogenation of l,2,3,4,4a/3,-5,8,8a/3-octahydronaphthalen-5a-ol-l ,4-dione acetate ( 2) over palladium-carbon or by oxidation of perhydro(4ad,8a0)naphthalene-la,4/3,5a-triol 5-acetate (5a) with chromic anhydride-1,4,4a/3,5,8,8a/3-Hexahydronaphthalen-la,4fl,5a-triol 5-Acetate ( 4).…”

“…11. Advantage was taken of the ease with which the tosyl grouping is eliminated, when the tosylate (5c) is treated with nucleophilic reagents, to remove the 1-substituent. Accordingly, the unsaturated diol ( 8), 1,2,3,5,6,7,8,-8a/3-octahydronaphthalene-l,S,8a-diol, was prepared by dissolving the tosylate (5c) in methanol containing potassium hydroxide. When 8, in the form of its diacetate, was hydrogenated in acetic acid in the presence of platinum, a saturated diol was obtained in moderate yield.…”

2α-Hydroxytestosterone diacetate

“…The crystal structure of 2~-hydroxytestosterone diacetate (2~,17fl-diacetoxy-4-androsten-3-one) was determined as part of an investigation of the solid and solution conformations of the A ring in 2-substituted A4-3-keto steroids. 2~-Hydroxytestosterone diacetate was obtained by repeated recrystallization, from methanol, of the acetoxylation products of 6flbromotestosterone acetate according to Clarke, Dobriner, Mooradian & Martini (1955), and suitable single crystals were also grown from methanol solution. X-ray diffraction measurements of the unit-cell parameters and intensities were carried out on a GE XRD-5 diffractometer.…”

Reaktionen mit Blei(IV)‐acetat, XVI. Eine neuartige Umwandlung von 2‐Acetoxy‐3‐oxo‐4,5‐epoxy‐steroiden

“…Sie wurde bis heutc in allen untcrsuchten Fallen der Bleitctraacetat-Oxydation von Epoxyketonen bcobachtet. Es handelt sich dabei um eine Analogie zur Dehydrierung von 3-0x0-d~-Verbindungen [9], die ebenfalls bei der Acctoxylierung rnittels Blci (1V)-acetat als Nebcnreaktion auftritt. lo [lo]) konnte ebenfalls isoliert werdenll).…”