摘要：
The formal synthesis of ()-morphine is described. The C-ring in morphine was prepared in an optically pure form from -glucal using Ferrier's carbocyclization reaction, and the vicinal tertiary and quaternary stereocenters in the C-ring were stereoselectively generated in a one-step reaction based on the cascade sequential Claisen rearrangement of an allylic vicinal diol derivative. After the one-step formation of the dibenzofuran structure, the intramolecular Friedel–Crafts type reaction effectively constructed the ABCE-phenanthrofuran skeleton. Introduction of a tosylamide function, followed by reductive cyclization furnished ()-dihydroisocodeine, the known synthetic intermediate for ()-morphine.Graphical abstractThe chiral and stereoselective synthesis of ()-dihydroisocodeine , the known synthetic intermediate of ()-morphine , is described. The vicinal tertiary and quaternary stereocenters in were effectively generated in one-step reaction based on the cascade sequential Claisen rearrangement of a cyclohexene-diol derived from -glucal.
展开
85
被折叠的 条评论
为什么被折叠?
到【灌水乐园】发言
