Abstract
UNSATURATED compounds are known to add, under the action of osmic acid, two hydroxyl groups at the place of their double bond1, these groups being in cis-exposition with regard to each other. The reaction course is analogous to that produced by KMnO4. However, action of the latter on cholesterol2 yields but 4–5 per cent of cis-cholestan-triol. Thus KMnO4 is unsuitable for the oxidation of the double bond in sterol-derived hormones, in particular in dehydro-androsterone.
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Details in the recent paper by Criegee, R., Ann., 522, 75 (1936), where the literature is cited.
Windaus, A., Ber., 40, 257 (1907).
Ushakov, M., and Lutenberg, A., “Dehydroandrosterone oxide”, in press in Journal Obshchei Chimii and Bull. Soc. Chim. de France.
Criegee (loc. cit.) mentions having obtained some cis-diols of the sterol group ; he does not give any details, nor mention what sterols he worked with.
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USHAKOV, M., LUTENBERG, A. Oxidation of Cholesterol and Dehydroandrosterone by Means of Osmic Acid. Nature 140, 466 (1937). https://doi.org/10.1038/140466b0
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DOI: https://doi.org/10.1038/140466b0
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