Palladium-Catalyzed Ortho-Arylation of Carbamate-Protected Estrogens
The palladium-catalyzed ortho-arylation of diethyl carbamate-protected estrone and estriol with aryl iodides gives the 2-arylated analogues. Subsequent removal of the carbamate directing group furnishes 2-arylated estrone, estradiol, or estriol depending on the method used.
Bedford, Robin B.,Brenner, Peter B.,Durrant, Steven J.,Gallagher, Timothy,Méndez-Gálvez, Carolina,Montgomery, Michelle
The synthesis of estriol 16- and 17-monoglucuronide from estriol
An efficient and convenient procedure for the synthesis of estriol 16- and 17-monoglucuronides from estriol is described. This is achieved by the selective protection and deprotection of the hydroxy groups in estriol, Koenigs-Knorr reactions with methyl 1-bromo-1-deoxy-2,3,4-tri-O-acetyl-α-D-glucopyranuronate and subsequent hydrolysis. The products have been characterized by proton nuclear magnetic resonance (1H NMR), two-dimensional 1H homonuclear shift-correlated spectra (2D-COSY) and mass spectra. The selective Koenigs-Knorr reaction of the alcoholic hydroxyl group in the presence of a phenolic hydroxyl group is also reported. Keywords: steroids; estriol; estriol 16- and 17-glucuronides; selective protection; Koenigs-Knorr reaction; synthesis.
Wu, Yinqiu,Blackwell, Leonard F.
p. 452 - 456
(2007/10/02)
An efficient method for selective acetylation of alcoholic hydroxyl groups
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Nagao,Fujita,Kohno,Yagi
p. 3202 - 3207
(2007/10/02)
Studies on steroid conjugates. XIII. Synthesis of 2,4,17α d3 estriol 3 glucuronoside