The synthesis of some analogues of morphine 6-glucuronide through Wittig reactions upon dihydrocodeinone

Abstract

In preliminary studies to establish the biological role of the glucuronide unit in morphine 6-glucuronide, a number of codeine derivatives bearing alkyl side chains appended through C-6 have been synthesised using Wittig reactions between suitable ylides and dihydrocodeinone. During the course of this work some aldolisation type products of dihydrocodeinone were obtained. Attempts to introduce side chains by radical coupling reactions between bromocodides and allyltributyltin failed.