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

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概要

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• 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.

• 公益社団法人日本薬学会の論文
• 1971-05-25

著者

• 青山 定夫

  Shionogi Research Laboratory Shionogi & Co. Ltd.

関連論文

• Linear Steroid Analogues. IV. Cyclization Reaction of 8,9-Seco-5α-androstane-8,9,11-trione Derivatives with Al_2O_3 and SiO_2
• Boron Trifluoride-catalyzed D-Homo Rearrangements of 20β-Acetoxy-5α-pregnanes
• Linear Steroid Analogues. III. Formation of Abeo-steroids from 3β, 20β-Diacetoxy-8,9-seco-5α-pregnane-8,9,11-trione
• Linear Steroid Analogues. II. Syntheses of Linear Progesterone and Testosterone Analogues
• Linear Steroid Analogues. I. Transformation of Steroid into Linear Steroid Analogues

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