Abstract
A new synthetic route leading to the titled compounds by three steps from estriol (I) has been developed. When estriol 3-benzoate (IIa) and methyl acetobromoglucuronate were stirred in benzene in the presence of silver carbonate, the condensation reaction occurred at C-16 and C-17 yielding two isomeric glucuronide derivatives (IIIa, IVa) in approximately equal amount. Upon alkaline hydrolysis these two were readily converted into the desired estriol monoglucuronides (V, VI). The structures of IIIa and IVa were further confirmed by transforming into the 16, 17-ketol derivatives (VII, VIII) by Jones oxidation. The yield and composition of the product in Koenigs-Knorr reaction were significantly influenced by the solvent as was shown in Table I. Application of the present method to the preparation of estriol-6, 7-3H 16-and 17-glucuronides has also been described.
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