signature=abcea710e8925522bb7987d7b1618edd,Formal synthesis of (-)-morphine from D-glucal based on t...

本文描述了()-吗啡的正式合成过程。通过Ferrier的碳环化反应从()-葡萄糖醛制备了光学纯的C环,并通过一锅法串联Claisen重排反应立体选择性地生成了C环内的三级和四级手性中心。随后,通过一连串的反应构建了ABCE-菲喃骨架。接着,引入对甲苯磺酰胺功能团,经过还原环化得到()-双氢异吗啡酮,这是()-吗啡的已知合成中间体。
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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.

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