Reactions of 14β, 15β-Epoxypregn-16-en-20-one with Nucleophiles
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概要
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The reactivities of the nucleophilic reagents such as alcohol, cyanide and thiol toward the △^<16>-double bond of 3β-acetoxy-14β, 15β-epoxy-5α-pregn-16-en-20-one (IV) have been investigated (Chart 1). All the nucleophiles showed the rear-side attack to provide the 16α-substituted derivatives. This result may be attributable to the characteristic feature of C/D-ring fusion, where ring D is less bent below than that of the ordinary 14β-steroid. Configuration of the 17-side chain of the adducts produced under the alkaline reaction conditions was found to be α. A possible explanation for the formation of the 16-cyano-14,16-diene (IX) from IV has also been described.
- 公益社団法人日本薬学会の論文
- 1968-11-25
著者
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南原 利夫
Pharmaceutical Institute, Tohoku University
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合屋 周次郎
Pharmaceutical Institute, Medical Faculty, University of Kyushu
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島田 和武
Pharmaceutical Institute, Tohoku University
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後藤 順一
Pharmaceutical Institute Tohoku University
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合屋 周次郎
Pharmaceutical Institute Tohoku University
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合屋 周次郎
Pharmaceutical Institute Medical Faculty University Of Kyushu
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南原 利夫
Pharmaceutical Institute Tohoku University
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