Abstract
ORGANIC chemists are well accustomed to spec tacular results from the researches of Prof. L. Ruzicka and his school. Yet the artificial production of the male sex hormone recorded in the October number of the Helvetica Chimica A eta by Ruzicka, Goldberg, Meyer, Briingger and Eichenberger prob ably transcends in interest any previous publication from the Zurich laboratories. Adopting the hypo thesis of Butenandt, who first isolated and charac terised the testicular hormone, that this substance is a hydroxyketone closely related to the sterols, Ruzicka and his collaborators examined the neutral fractions arising from the chromic acid oxidation of the acetate of dihydrocholesterol and some of its stereoisomerides. The removal of the sterol side chain by such oxidations has long been used for the identification of the side chain, but previous investi gators had been unable to isolate the major fragment of the molecule. This has been achieved by Ruzicka, and the hydroxyketone resulting from epi-hydro cholesterol proved to be completely identicalwitft the male hormone (androsterone) isolated by Butenandt. By this simple experiment, the structure of a complex natural product has been completely elucidated and its stereochemical relationship to the sterols established. Apart from speculation, the only previous chemical knowledge of the hormone was that it was a saturated hydroxyketone of the probable formula C19H30O2. It is unfortunate that this con version of cholesterol into androsterone should be described by the investigators as a ‘synthesis’.
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The Male Sex Hormone. Nature 134, 563 (1934). https://doi.org/10.1038/134563b0
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DOI: https://doi.org/10.1038/134563b0
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