Abstract
The A-ring monoglucuronides and monosulfates of 4-hydroxyesteriol were synthesized from 4-hydroxyestriol 16, 17-diacetate by means of the Koenigs-Knorr reaction with methyl α-acetobromoglucuronate and sulfation with sulfur trioxide-pyridine complex, respectively. The conjugated positions of these compounds were unequivocally elucidated by leading the products to guaiacol estrogens. The D-ring monoglucuronides and monosulfates of 4-hydroxyestriol were also obtained from 4-hydroxyestriol 3, 4-dibenzyl ether by glucuronidation and sulfation followed by hydrogenolysis, respectively. The conjugated positions were established on the basis of spectral data of derivatives. The preparation of 4-hydroxyestradiol 17-conjugates is also described.
