New routes to a-ring substituted estrogens.
Estrogens can be regiospecifically functionalized at the position 2 by a few electrophilic reagents. Reactions of estradiol 3-methyl ether-17 beta-acetate with Hg(OAc)2 and BF3 . Et2O/Ac2O allows the preparation of 2-chloromercurio- and 2-organoboron-derivatives respectively. Both the above compounds are useful starting material for easy preparations of 2-catecholestrogens and 2-chloromercurio-derivative can be transformed in other functionalized estrogens. New procedures for the preparation of 2,4-dinitroestrone and 2-nitroestrone are also described.
D003903:Deuterium; D045166:Estradiol Congeners / Q000138:chemical synthesis*; D002393:Estrogens, Catechol / Q000138:chemical synthesis; D007202:Indicators and Reagents; D013329:Structure-Activity Relationship
D045166:Estradiol Congeners; D002393:Estrogens, Catechol; D007202:Indicators and Reagents; D003903:Deuterium