Molecules 2005, 10(3), 572-582; doi:10.3390/10030572
Article

Epoxidation and Reduction of DHEA, 1,4,6-Androstatrien-3-one and 4,6-Androstadien-3β,17β-diol

Received: 1 July 2004; in revised form: 26 February 2005 / Accepted: 1 March 2005 / Published: 25 May 2005
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.
Abstract: Dehydroepiandrosterone (DHEA) reacted with m-chloroperoxybenzoic acid(m-CPBA) to form 3β-hydroxy-5α,6α-epoxyandrostan-17-one (1), but it did not reactwith 30% H2O2. 1,4,6-Androstatrien-3,17-dione (2) was obtained from DHEA and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in dioxane. Compound 2 was reacted with 30%H2O2 and 5% NaOH in methanol to give 1α,2α-epoxy-4,6-androstadien-3,17-dione (3),which was stereoselectively reduced with NaBH4 to form 1α,2α-epoxy-4,6-androstadien-3β,17β-diol (7) and reacted with Li metal in absolute ethanol-tetrahydrofuran mixture togive 2-ethoxy-1,4,6-androstatrien-3,17-dione (8). Compound 2 was also epoxidized withm-CPBA in dichloromethane to afford 6α,7α-epoxy-1,4-androstadien-3,17-dione (4),which was reacted with NaBH4 to synthesize 6α,7α-epoxy-4-androsten-3β,17β-diol (9).Compound 4 was reduced with Li metal in absolute ethanol-tetrahydrofuran mixture toform 7β-ethoxy-6α-hydroxy-1,4-androstadien-3,17-dione (10). Compound 2 was reducedwith NaBH4 in absolute ethanol to form 4,6-androstadien-3β,17β-diol (5), which wasreacted with 30% H2O2 to give the original compound, but which reacted with m-CPBAto give 4β,5β-epoxy-6-androsten-3β,17β-diol (6).
Keywords: Dehydroepiandrosterone; position selective and reagent selective epoxidation and reduction; H2O2; m-chloroperoxybenzoic acid; sodium borohydride; lithium
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MDPI and ACS Style

Ma, E.; Kim, E. Epoxidation and Reduction of DHEA, 1,4,6-Androstatrien-3-one and 4,6-Androstadien-3β,17β-diol. Molecules 2005, 10, 572-582.

AMA Style

Ma E, Kim E. Epoxidation and Reduction of DHEA, 1,4,6-Androstatrien-3-one and 4,6-Androstadien-3β,17β-diol. Molecules. 2005; 10(3):572-582.

Chicago/Turabian Style

Ma, Eunsook; Kim, Eunjeong. 2005. "Epoxidation and Reduction of DHEA, 1,4,6-Androstatrien-3-one and 4,6-Androstadien-3β,17β-diol." Molecules 10, no. 3: 572-582.

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