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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References
- 1.
Details in the recent paper by Criegee, R., Ann., 522, 75 (1936), where the literature is cited.
- 2.
Windaus, A., Ber., 40, 257 (1907).
- 3.
Ushakov, M., and Lutenberg, A., “Dehydroandrosterone oxide”, in press in Journal Obshchei Chimii and Bull. Soc. Chim. de France.
- 4.
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.
Author information
Affiliations
Laboratory of Sterol and Hormone Chemistry, All-Union Institute of Experimental Medicine, Moscow.
- M. USHAKOV
- & A. LUTENBERG
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Further reading
-
New case of closure of a 5?, 6?-oxide ring in the androstane series
Bulletin of the Academy of Sciences of the USSR Division of Chemical Science (1960)
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