24302-58-7Relevant academic research and scientific papers
EPOXIDATION OF ESTRA-5(10),9(11)-DIENE DERIVATIVES; A CONVENIENT SYNTHESIS OF 11Β-VINYLESTRONE ACETATE
Napolitano, Elio,Fiaschi, Rita,Hanson, Robert N.
, p. 323 - 326 (2007/10/02)
The title compound has been prepared from 17β-hydroxyestra-4,9(10)-dien-3-one, 1, in a sixstep synthesis requiring only one purification and providing a 58percent overall yield.The key steps of the synthesis are the regio- and stereo-selective epoxidation of 3,3:17,17-bis(ethylenedioxy)-estra-5(10),9(11)-diene, 2e, to yield the corresponding 5α,10α-epoxide derivative using hydrogen peroxide and hexafluoroacetone, followed by the copper(I)-catalyzed conjugate opening of the vinyl epoxide by vinylmagnesium bromide.A variety of extra-5(10),9(11)-diene derivatives differing for substitution at C-17 were also regio- and stereo-selectively epoxidized.
