Steroid Series. XXI. Reaction of 4-Halo-Δ^4-3-oxosteroides with Dimethyl Sulfoxide
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概要
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The reaction of 4-chloro-Δ^4-3-oxosteroids (Ia, c, e) with dimethyl sulfoxide were shown to yield Δ^<4,6>-3-oxosteroids (IIg, h, i). These were accompanied by the 3,6-dione (III) and Δ^4-3,6-dione (IV) in the case of 19-methylsteroid, by estra-1,3,5 (10)-triene-3,17β-diol 17-acetate (VII) from 19-norsteroid, and by Δ^4-3-oxo-6β, 19-oxide (VI) from 19-hydroxymethylsteroid. With dimethylsulfoxide 4-bromo-Δ^4-3-oxosteroids (Ib, d, f) gave the 4-bromo-Δ^<4,6>-3-oxosteroids (IIb, d, V) under the same reaction conditions. Bromination of 17β-acetoxyandrosta-4,6-dien-3-one (IIg) in dimethylsulfoxide afforded the bromotrienone (X), the 2α-bromo (VIII) and 2,2-dibromo (IX)-derivatives of IIg being intermediates in the conversion.
- 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