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Issue 12, 1994
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Synthesis of deuterium-labelled medroxyprogesterone, megestrol and melengestrol derivatives

Abstract

The deuterium-labelled medroxyprogesterone derivatives 1 and 2, were prepared by opening of the epoxide in 5β, 6β-epoxy-17α-hydroxypregnane-3,20-dione 3,20-bis(ethyleneketal)(9β) with [2H3]methyl magnesium iodide and further processing of the thus obtained 6-C-pregnane derivative, 10. [2H3]megestrol acetate (4) was prepared by p-chloranil oxidation of [2H3]medroxyprogesterone acetate (2). Subsequent deacetylation of 4 gave [2H3]megestrol (3). In a similar fashion, 16-dehydro-16-methylprogesterone (11) was converted into [2H3]melengestrol (5) and its acetate, 6. In addition, the application of the labelled steroids in the detection of gestagens in samples of kidney fat was shown.

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Article type: Paper
DOI: 10.1039/AN9941902645
Analyst, 1994,119, 2645-2650

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    Synthesis of deuterium-labelled medroxyprogesterone, megestrol and melengestrol derivatives

    P. Smid, M. Jacquemijns, P. W. Zoontjes, E. A. I. M. Evers, R. W. Stephany, J. F. C. Stavenuiter, L. A. van Ginkel and G. Zomer, Analyst, 1994, 119, 2645
    DOI: 10.1039/AN9941902645

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