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DOI: 10.1039/A709186I (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1998, 1967-1972

Synthesis of 4-hydroxyestrogens from steroid 4,5-epoxides: thermal rearrangement of 4-chloro-4,5-epoxides

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Helena Majgier-Baranowska, John N. Bridson, Kirk Marat and John F. Templeton

Abstract

The synthesis of 4-hydroxyestrone and 4-hydroxyestradiol from estr-4-ene-3,17-dione through the 4,5-epoxyestra-3,17-diones is described. Thermolysis of 4-chloro-4,5-epoxyestra-3,17-diones also gives 4-hydroxyestrone, but in lower yield, together with 4-hydroxyestra-4,6-diene-3,17-dione and the B ring aromatic product, estra-5,7,9-triene-4,17-dione. Structures have been established by NMR methods except for the structure of 4β-chloro-4,5-epoxy-5α-estra-3,17-dione which has been determined by X-ray crystallographic analysis.

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