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Upon treatment of 25(R)-spirost-5-en-3ÃŽÂ²-ol (diosgenin), 25(R)-1,4,6-spirostatrien-3-one and 25(R)-4,6-spirostadien-3ÃŽÂ²-ol with 30% H2O2 and 5% NaOH in methanol, diosgenin did not react, 25(R)-1,4,6-spirostatrien-3-one was converted to 25(R)-1ÃŽÂ±,2ÃŽÂ±-epoxy-4,6-spirostadien-3-one and 25(R)-4,6-spirostadien-3ÃŽÂ²-ol was oxidized to give a small amount of 25(R)-4,6-spirostadien-3-one, while most of the original starting material remained unchanged. On the other hand, reactions of diosgenin, 25(R)-1,4,6-spirostatrien-3-one and 25(R)-4,6-spirostadien-3ÃŽÂ²-ol with m-chloroperoxybenzoic acid in chloroform yielded 25(R)-5ÃŽÂ±,6ÃŽÂ±-epoxyspirostan-3ÃŽÂ²-ol, 25(R)-6ÃŽÂ±,7ÃŽÂ±-epoxy-1,4-spirostadien-3-one and 25(R)-4ÃŽÂ²,5ÃŽÂ²-epoxy-6-spirosten-3ÃŽÂ²-ol, respectively

Epoxidation of Diosgenin, 25(R)-1,4,6-Spirostatrien-3-one and 25(R)-4,6-Spirostadien-3β-ol