{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,18]],"date-time":"2025-10-18T10:24:55Z","timestamp":1760783095180,"version":"build-2065373602"},"reference-count":35,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2005,5,25]],"date-time":"2005-05-25T00:00:00Z","timestamp":1116979200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Dehydroepiandrosterone (DHEA) reacted with m-chloroperoxybenzoic acid(m-CPBA) to form 3\u03b2-hydroxy-5\u03b1,6\u03b1-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 1\u03b1,2\u03b1-epoxy-4,6-androstadien-3,17-dione (3),which was stereoselectively reduced with NaBH4 to form 1\u03b1,2\u03b1-epoxy-4,6-androstadien-3\u03b2,17\u03b2-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 6\u03b1,7\u03b1-epoxy-1,4-androstadien-3,17-dione (4),which was reacted with NaBH4 to synthesize 6\u03b1,7\u03b1-epoxy-4-androsten-3\u03b2,17\u03b2-diol (9).Compound 4 was reduced with Li metal in absolute ethanol-tetrahydrofuran mixture toform 7\u03b2-ethoxy-6\u03b1-hydroxy-1,4-androstadien-3,17-dione (10). Compound 2 was reducedwith NaBH4 in absolute ethanol to form 4,6-androstadien-3\u03b2,17\u03b2-diol (5), which wasreacted with 30% H2O2 to give the original compound, but which reacted with m-CPBAto give 4\u03b2,5\u03b2-epoxy-6-androsten-3\u03b2,17\u03b2-diol (6).<\/jats:p>","DOI":"10.3390\/10030572","type":"journal-article","created":{"date-parts":[[2008,10,25]],"date-time":"2008-10-25T13:32:11Z","timestamp":1224941531000},"page":"572-582","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Epoxidation and Reduction of DHEA, 1,4,6-Androstatrien-3-one and 4,6-Androstadien-3\u03b2,17\u03b2-diol"],"prefix":"10.3390","volume":"10","author":[{"given":"Eunsook","family":"Ma","sequence":"first","affiliation":[{"name":"College of Pharmacy, Catholic University of Daegu, Hayang, 712-702, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Eunjeong","family":"Kim","sequence":"additional","affiliation":[{"name":"College of Pharmacy, Catholic University of Daegu, Hayang, 712-702, Korea"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2005,5,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"649","DOI":"10.1016\/0022-4731(87)90133-6","article-title":"Neurosteroids: 3\u03b2-hydroxy-\u03945-derivatives in rat and monkey brain","volume":"27","author":"Robel","year":"1998","journal-title":"J. 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