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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

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Received: 18 September 2003; in revised form: 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 which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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(12):886-893.

Chicago/Turabian Style

Ma, Eunsook; Kim, Jongwon. 2003. "Epoxidation of Diosgenin, 25(R)-1,4,6-Spirostatrien-3-one and 25(R)-4,6-Spirostadien-3β-ol." Molecules 8, no. 12: 886-893.


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