Collect. Czech. Chem. Commun. 1982, 47, 3148-3159

Desulfuration of steroidal thians

Alexander Kasal

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


The reaction of 4-thia-5-cholesten-3-one (X) with Raney nickel in protic medium affords alcohol III, while A-nor-5β-cholestan-3-one (XXIII), A-bisnor-2,5-secocholestane (XXXI) and the esters of the type XVIII are formed as by-products. When aprotic medium is used compounds XXIII and XXXI are the main products. During desulfuration with a less active Raney nickel the mentioned substances are accompanied by 5-unsaturated derivatives of the type I, XIV and XXIX. Optimum conditions for the preparation of either saturated alcohols of type III or of unsaturated esters of type XIV were found.