Reactions of 5α, 14β-Pregn-16-en-20-one with Nucleephiles

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3Β, 17α-Dihydroxy-5α, 14β-pregnan-20-one (III) and 3β-hydroxy-5α, 14β-pregn-16-en-20-one (VII) were prepared from 14β-isoandrosterone (I) by way of the 17β-ethynyl-17α-hydroxy derivative (II) in satisfactory yield. The reactivities of the nucleophilic reagents such as potassium cyanide, thioacetic acid, ethylenimine and nitromethane toward the Δ16-20-ketone system in VII have been investigated. All these nucleophiles showed the β-side attack yielding the 16β-substituted derivatives, in which the configuration of the side chain at C-17 was α. These results may be ascribable to the characteristic feature of C/D-ring fusion forming the cage-like structure.

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