Abstract
The oxidation of 3β-acetoxycholesta-5,7-diene (1) with potassium permanganate–sodium periodate reagent gave epoxy-diol 2 with almost quantitative yield. Similar oxidation of cholesta-2,4-diene (3) afforded, as well as epoxy-diols 5 and 6, products of cleavage of the double bonds. These results show that formation of epoxy-diols predominates in the case of hindered steroidal dienes (e.g., diene 1), whereas oxidation of unhindered steroidal dienes (e.g., diene 2) gives, in addition to epoxy-diols, products of cleavage of the double bonds.
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