28839-09-0

Upstream product

• 6218-29-7 17β-hydroxyestra-4,9-dien-3-one 
• 53303-91-6 (8S,13S,14S,17S)-13-methyl-1,2,4,6,7,8,12,13,14,15,16,17-dodecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-17-ol 
• 98-88-4 benzoyl chloride 

Downstream Products

• 24275-27-2 17β-benzoyloxy-3,3-ethylenedioxy-5α,10α-oxidoestr-9(11)-ene 
• 24302-58-7 17β-benzoyloxy-3,3-ethylenedioxy-5β,10β-oxidoestr-9(11)-ene 

Relevant academic research and scientific papers

EPOXIDATION OF ESTRA-5(10),9(11)-DIENE DERIVATIVES; A CONVENIENT SYNTHESIS OF 11Β-VINYLESTRONE ACETATE

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.