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Molecules 2003, 8(12), 886-893; doi:10.3390/81200886
Article

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

*  and
College of Pharmacy, Catholic University of Daegu, Hayang, 712-702, Korea
* Author to whom correspondence should be addressed.
Received: 18 September 2003 / Revised: 12 December 2003 / Accepted: 18 December 2003 / Published: 31 December 2003
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Abstract

Upon treatment of 25(R)-spirost-5-en-3β-ol (diosgenin), 25(R)-1,4,6-spirostatrien-3-one and 25(R)-4,6-spirostadien-3β-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)-1α,2α-epoxy-4,6-spirostadien-3-one and 25(R)-4,6-spirostadien-3β-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-3β-ol with m-chloroperoxybenzoic acid in chloroform yielded 25(R)-5α,6α-epoxyspirostan-3β-ol, 25(R)-6α,7α-epoxy-1,4-spirostadien-3-one and 25(R)-4β,5β-epoxy-6-spirosten-3β-ol, respectively.
Keywords: Diosgenin; Stereoselective epoxidation; H2O2; m-Chloroperoxybenzoic acid Diosgenin; Stereoselective epoxidation; H2O2; m-Chloroperoxybenzoic acid
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Ma, E.; Kim, J. Epoxidation of Diosgenin, 25(R)-1,4,6-Spirostatrien-3-one and 25(R)-4,6-Spirostadien-3β-ol. Molecules 2003, 8, 886-893.

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