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Issue 0, 1987
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Synthesis of ring-A and -B substituted 17α-acetoxypregnan-20-one derivatives with potential activity on the digitalis receptor in cardiac muscle

Abstract

The synthesis of C-6 substituted (methyl, hydroxy, acetoxy, methoxy, ethoxy, methoxycarbonyloxy, ethoxycarbonyloxy, fluoro, chloro, bromo) 5α,5β,C-4 unsaturated and C-4,6 unsaturated derivatives of 17α-acetoxypregn-4-ene-3,20-dione (17α-acetoxyprogesterone) are reported. A convenient synthesis of 6α-hydroxy derivatives by selective reduction of the 4-ene-3,6-dione system is described as is the formation of 6α-alkoxycarbonyl derivatives. Synthesis of a 5α-hydroxy-6-ketone via the 5β,6β-epoxide with N-bromosuccinimide is reported. A new preparation of 3α-hydroxy-5α-derivatives from the 4-en-3-one group has been carried out. 1H n.m.r. spectra are recorded. These compounds were synthesized to test for ouabain displacement activity on the digitalis receptor in cardiac muscle.

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Article type: Paper
DOI: 10.1039/P19870001361
J. Chem. Soc., Perkin Trans. 1, 1987, 1361-1368

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    Synthesis of ring-A and -B substituted 17α-acetoxypregnan-20-one derivatives with potential activity on the digitalis receptor in cardiac muscle

    J. F. Templeton, V. P. S. Kumar, R. S. Kim and F. S. LaBella, J. Chem. Soc., Perkin Trans. 1, 1987, 1361
    DOI: 10.1039/P19870001361

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