Collect. Czech. Chem. Commun. 2005, 70, 507-518

Synthesis, Reactions, Conformation Analysis, and NMR Spectra of 5,10-Epoxy-5ξ,10ξ-estrane-3,17-diones

Miloš Buděšínský, Jan Fajkoš, Jaroslav Günter and Alexander Kasal*

Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic


On epoxidation of estr-5(10)-ene-3,17-dione, the 5β,10β-epoxide is the major product. The mixture of epoxides was converted into 5,10β-dihydroxy-5α-estrane-3,17-dione, 10α- and 10β-hydroxyestr-4-ene-3,17-dione, and estrone. Due to the sensitivity of the products, 1H NMR was the best way to monitor the reaction pathway.

Keywords: Steroids; Epoxidation; Epoxide cleavage; Stereoselective reactions; Conformation analysis; NMR spectroscopy.

References: 13 live references.