SYNTHESIS OF 4-HYDROXYESTROGENS FROM STEROID 4,5-EPOXIDES - THERMAL REARRANGEMENT OF 4-CHLORO-4,5-EPOXIDES

Authors
MAJGIERBARANOWSKA H BRIDSON JN MARAT K TEMPLETON JF
Citation
H. Majgierbaranowska et al., SYNTHESIS OF 4-HYDROXYESTROGENS FROM STEROID 4,5-EPOXIDES - THERMAL REARRANGEMENT OF 4-CHLORO-4,5-EPOXIDES, Journal of the Chemical Society. Perkin transactions. I (Print), (12), 1998, pp. 1967-1972
Citations number
26
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of the Chemical Society. Perkin transactions. I (Print) → ACNP
ISSN journal
0300922X
Issue
12
Year of publication
1998
Pages
1967 - 1972
Database
ISI
SICI code
0300-922X(1998):12<1967:SO4FS4>2.0.ZU;2-P
Abstract
The synthesis of 4-hydroxyestrone and 4-hydroxyestradiol from estr-4-e ne-3,17-dione through the 4,5-epoxyestra-3,17-diones is described. The rmolysis of 4-chloro-4,5-epoxyestra-3,17-diones also gives 4-hydroxyes trone, 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 struct ure of 4 beta-chloro-4,5-epoxy-5 alpha-estra-3,17-dione which has been determined by X-ray crystallographic analysis.