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Issue 1, 1982
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The solution conformation of 17α-acetoxy-6α-methylprogesterone (‘medroxyprogesterone acetate’) : use of circular dichroism, nuclear overhauser effect difference and two-dimensional J spectroscopy

Abstract

17α-Acetoxy-6α-methylprogesterone, which is known from X-ray crystallographic study to have the inverted (1β,2α) half-chair conformation of ring A in the solid state, exhibits c.d. in solution which is normal for a steroidal 4-en-3-one, but the c,d. in the crystal shows inverted sign in the n→π* band. The inference that the solution conformation is of normal type, approximizing to the 1α,2β-half-chair, is supported by a 1H n.m.r. study at 400 MHz. Application of n.o.e. difference and two-dimensional J techniques permitted a full assignment of all 1H chemical shifts and geminal and vicinal coupling constants. These parameters for the protons at C-1 and -2, together with the n.o.e. observations, establish that the preferred conformation of ring A is normal in a variety of solvents.

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Article type: Paper
DOI: 10.1039/P29820000105
J. Chem. Soc., Perkin Trans. 2, 1982, 105-110

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    The solution conformation of 17α-acetoxy-6α-methylprogesterone (‘medroxyprogesterone acetate’) : use of circular dichroism, nuclear overhauser effect difference and two-dimensional J spectroscopy

    M. W. Barrett, R. D. Farrant, D. N. Kirk, J. D. Marsh, J. K. M. Sanders and W. L. Duax, J. Chem. Soc., Perkin Trans. 2, 1982, 105
    DOI: 10.1039/P29820000105

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