Steroid Series. XX. Reaction of α, β-Epoxyketone with Dimethyl Sulfoxide
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概要
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The oxidation of 17β-hydroxy-4β, 5-epoxy-5α-androstan-3-one (I) and its 4α, 5α-isomer (II) with dimethyl sulfoxide gave 4,17β-dihydroxyandrost-4-en-3-one (IV), 17β-hydroxyandrosta-1,4-dien-3-one (V), 2,17β-dihydroxyandrosta-1,4-dien-3-one (VI) and 2α, 17β-dihydroxyandrost-4-en-3-one (VII). The same reaction of 17β-acetoxy-4β, 5-epoxy-19-nor-5β-androstan-3-one (IIIa) afforded 4,17β-dihydroxy-19-norandrost-4-en-3-one 17-acetate (VIIIa), estra-1,3,5 (10)-triene-3,17β-diol 17-acetate (IX) and estra-1,3,5 (10)-triene-2,3,17β-triol 17-acetate (X). The corresponding 19-oxosteroid (IIIb) yielded the estrane derivatives (IX and X), while 19-hydroxymethyl steroid (IIIc) gave, in addition to the estrane derivatives (IX and X), 4,17β, 19-trihydroxyandrost-4-en-3-one 17-acetate (VIIIc) and 17β-acetoxy-2β, 19-oxidoandrost-4-en-3-one (XI).
- 公益社団法人日本薬学会の論文
- 1969-06-25
著者
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森沢 靖弘
Central Research Laboratories Sankyo Co. Ltd.
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田部 克巳
Central Research Laboratories, Sankyo Co., Ltd.
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田部 克巳
Central Research Laboratories Sankyo Co. Ltd.
関連論文
- Steroid Series. XVII. New Synthetic Routes to 19-Norsteroids (1)
- Steroid Series. XVI. The Preparation of 3α, 5α-Cyclo-6β, 19-oxidosteroids and its Conversion to 19-Oxygenated Steroid Derivatives
- Steroid Series. X. Ozonolysis of 7-Oxo-⊿^5-Steroids. An Attempt to synthesize 6-Azasteroid Hormone Analogs.
- The Formation of 6,19-Epoxy-3,5-cyclo-steroid
- Steroid Series. VI. : Synthesis of B-Norsteroids. (2).
- Steroid Series. V. : Synthesis of B-Norsteroids. (1).
- Steroid Series. IV. : Ozonization of Cyclic 3-(Ethylene Acetal) of ⊿^4-3-oxosteroids.
- Steroid Series. III. : Ozonization of 3-Acetoxy-⊿^5-steroids in the Presence of Formaldehyde.
- 7-Aza-5β-cholestane Derivatives
- Steroid Series. XI. Synthesis of B-Norsteroid.
- Steroid Series. IX. A New Route to 6-Nitrosteroid Derivatives.
- The Structure of Alantolactone. III. Configurations of 4-Methyl Group in Tetrahydroalantolactone and Several 3-Hydroxytetrahydroalantolactones.
- The Structure of Alantolactone. II. The Conversion of Alantolactone into Dihydroeudesmol.
- Steroid Series. XXI. Reaction of 4-Halo-Δ^4-3-oxosteroides with Dimethyl Sulfoxide
- Steroid Series. XX. Reaction of α, β-Epoxyketone with Dimethyl Sulfoxide
- Steroid Series. XIII. Stereochemistry of B-Nor-5α-and -5β-6-oxocholestane Derivatives
- Steroid Series. XII. Stereochemistry of B-Nor-5β, 8α-steroid Derivatives
- 19-酸素化ステロイドの化学 : 19-ノルステロイドの合成