Linear Steroid Analogues. III. Formation of Abeo-steroids from 3β, 20β-Diacetoxy-8, 9-seco-5α-pregnane-8, 9, 11-trione

Autor:	Sadao Aoyama
Rok vydání:	1971
Předmět:	chemistry.chemical_classification Ketone Chemistry Silica gel Stereochemistry medicine.medical_treatment Pregnane General Chemistry General Medicine Ring (chemistry) Steroid Catalysis chemistry.chemical_compound Drug Discovery medicine
Zdroj:	Chemical and Pharmaceutical Bulletin. 19:896-905
ISSN:	1347-5223 0009-2363
Popis:	A small amount of 3β, 20β-diacetoxy-9 (8→7)-abeo-5α-pregn-7 (9)-ene-8, 11-dione (4), a compound with a 6-5-7-5 ring system, was formed in the alumina catalyzed cyclization of 3β, 20β-diacetoxy-8, 9-seco-5α-pregnane-8, 9, 11-trione (1). As it was not at first possible to isolate 4 in a pure state, the structure was deduced from a derivative, the saturated ketone (10), the structure of which was confirmed by its synthesis from the known glycol monomesylate (9b) with a 6-6-6-5 ring system by means of the pinacolic type rearrangement. Later, the compounds (4a, b) were obtained by cyclization of 1 with silica gel followed by alumina treatment and all the features of the reaction were clarified. The stereochemistry of the ketone (10) and its derivatives was also discussed.
Databáze:	OpenAIRE
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