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Epoxidation and Reduction of DHEA, 1,4,6-Androstatrien-3-one and 4,6-Androstadien-3β,17β-diol
College of Pharmacy, Catholic University of Daegu, Hayang, 712-702, Korea
* Author to whom correspondence should be addressed.
Received: 1 July 2004; in revised form: 26 February 2005 / Accepted: 1 March 2005 / Published: 25 May 2005
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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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.
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.
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.