INVESTIGATIONS ON STEROIDS. XI. NEW TRANSFORMATION PRODUCTS OF STROPHANTHIDIN: STUDIES ON ETHYL 3(β),5,19-TRIHYDROXYETIOCHOLANATE¹

INVESTIGATIONS ON STEROIDS. XXII. STUDIES ON OUABAGENIN. I*

“…As is known from sugar chemistry, primary alcohol groups react more readily with triphenyl chloromethane than do secondary ones, to form ethers which are stable towards alkali but are easily hydrolyzed by acids. As was shown in this laboratory (27), treatment of ethyl 3/3,5,19-trihydroxyetianate, a degradation product of strophanthidol, with a stoichiometric amount (1.1 equivalents) of triphenylchloromethane yields as the main reaction product 19-tritoxy-3/3,5dihydroxyetianate, accompanied by a small amount of ethyl 3/3,19-ditritoxy-5hydroxyetianate. By acetylation and subsequent detritylation of the main product, ethyl 3|3-acetoxy-5,19-dihydroxyetianate was obtained.…”

INVESTIGATIONS ON STEROIDS. XIII. TRANSFORMATION OF STROPHANTHIDIN INTO COMPOUNDS STRUCTURALLY RELATED TO STEROID HORMONES1

“…Previously (1) an attempt was made to subject I to selective oxidation either The compound proven in the present paper to possess structure XI {vide supra) is different from the previously described (1) substance to which had been tentatively assigned the same formula. Hence a reinvestigation of the latter substance was indicated.…”

INVESTIGATIONS ON STEROIDS. XII. NEW STEROIDS DERIVED FROM STROPHANTHIDOL: ETHYL 3β,5-DIHYDROXY-8, 19-OXIDOETIOCHOLANATE AND TRANSFORMATION PRODUCTS1

“…Thus a large amount of neutral mother liquors had accumulated. With a view to obtaining substantial quantities of the compound now considered to be ethyl 3/3,5-dihydroxy-8,19-oxidoetiocholanate (VI), they were subjected to 1 This investigation was supported by research grants from Sharp and Dohme, Inc. in Philadelphia and from the National Cancer Institute of the National Institutes of Health, Public Health Service. Presented before the Division of Medicinal Chemistry at the 118th Meeting of the American Chemical Society in Chicago, September 6, 1950. [cf.…”