Oxidation of androsta-3,5- and 4,6-dienes by the biphasic system potassium permanganate:copper sulfate afforded the 3α,4α-epoxy-5α-hydroxy-6-ketone and the 5α,6α-epoxy-4β-hydroxy-7-ketone respectively as the major products whilst the androsta-3,5-dien-7-one and androsta-4,6-dien-3-one gave the 3α,4α- and 6α,7α-epoxides as the major products.
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