Journal
MONATSHEFTE FUR CHEMIE
Volume 132, Issue 3, Pages 387-392Publisher
SPRINGER-VERLAG WIEN
DOI: 10.1007/s007060170124
Keywords
anti-hormones; mifepristone; NMR spectroscopy; oxidation; cancer therapy
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Selenium dioxide oxidation allows the selective introduction of a hydroxyl group at position 6 of the steroid skeleton of the antihormone (11 beta, 17 beta)-11-(4-dimethylamino-phenyl)-17-hydroxyl- 17-( 1-propynyl)-estra-4,9-dien-3-one (mifepristone, RU 486) and leads in a one-step procedure to two diastereomeric oxidation products. Their structure (6 alpha- and 6 alpha -hydroxy-mifepristone) was determined by NMR spectroscopy. The antiprogestinic activity of the oxidation products is comparable to that of mifepristone.
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