Total Synthesis of 13β-Allylgonanes. I. Synthesis of dl-17α-Ethynyl-17β-hydroxy-13β-allylgon-4-en-3-one
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概要
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dl-17α-Ethynyl-17β-hydroxy-13β-allylgon-4-en-3-one (XXIV) was synthesized via 17β, 2'-epoxy pentaene (X). The double bonds at C-14 and -8 of X was hydrogenated sequentially by conventional methods. 17β, 2'-Epoxy triene (XIII) was treated with p-toluenesulfonic acid in acetic anhydride to give 13β-allylgonane (XIV) as a major product. Birch reduction of the tetrahydropyranyl ether (XIX) followed by acid treatment yielded the 4-en-3-one compound (XXI), which was oxidized with chromium trioxidepyridine complex to the 17-ketone (XXII). The enol ether (XXIII) was treated with lithium acetylide in ethylenediamine, and then with acid to yield XXIV. The progestational activity of XXIV is as potent as norgestrel.
- 社団法人日本薬学会の論文
- 1973-10-25
著者
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吉岡 晃一
Central Research Division, Takeda Chemical Industries, Ltd.
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吉岡 晃一
Central Research Division Takeda Chemical Industries Ltd.
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平賀 謙太郎
武田薬品工業株式会社中央研究所
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平賀 謙太郎
Chemical Research Laboratories Research & Development Division Takeda Chemical Industries Ltd.
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後藤 義一
Chemistry Research Laboratories
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後藤 義一
武田薬品工業(株)中央研究所
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三木 卓一
武田薬品工業株式会社中央研究所
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吉岡 晃一
Chemical Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.
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三木 卓一
Chemical Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.
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朝子 典彦
Chemical Research Laboratories, Central Research Division, Takeda Chemical Industries, Ltd.
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