1968 Volume 16 Issue 11 Pages 2114-2119
The first synthesis of three glucuronides of narcotics was reported. Codeine glucuronide (Va) was prepared by the condensation of codeine (Ia) with acetobromo sugar derivative (II) in the presence of silver carbonate and the following removal of the protecting groups by solvolysis and hydrolysis with sodium methoxide and aq. barium hydroxide, respectively. Morphine-6-glucuronide (Vb) was synthesized similarly to Va utilizing 3-acetyl-morphine (Ib) as the starting material. Morphine-3-glucuronide (VIII) was prepared by the condensation of morphine (VI) with II in sodium hydroxide-acetone. In this reaction, the intermediate derivative (VII) was not obtained but hydrolyzed to the free glucuronide (VIII).