Angular substituted polycyclic compounds,pt.2

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  • Angular Substituted Polycyclic Compounds. II. Reaction of Cholest-4-en-3-one with Metallic Cyano Complexes.

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Cyanation of cholest-4-en-3-one (I) was attempted with CN-Mg-I, Li[Al(CN)4], H[Al(tert-BuO)3CN], and H[Al(iso-PrO)8CN] respectively to give the cyano ketone compounds, but in the case of H[Al(iso-PrO)3CN], 1, 3-cyanohydrins were obtained. The reduction of epimeric 3-oxo-cholestane-5-carbonitrile with aluminum isopropoxide and with sodium borohydride afforded the four cyanohydrins which were designated as the formulae (VIII), (VII), (XII), and (XIII).

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