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(-)-可待因的简洁全合成。

Concise Total Synthesis of (-)-Codeine.

机构信息

Department of Chemical Sciences, Indian Institute of Science Education and Research Kolkata, Mohanpur Campus, Kalyani, Nadia 741 246, West Bengal, India.

Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhauri, Bhopal 462 066, Madhya Pradesh, India.

出版信息

J Org Chem. 2024 Sep 6;89(17):12485-12497. doi: 10.1021/acs.joc.4c01452. Epub 2024 Aug 20.

Abstract

Codeine and morphine are among the few natural products that are used directly as drugs for medical treatment. However, the availability of these is widely dependent on natural resources. Herein, we report an efficient enantioselective seven-step synthesis of (-)-codeine starting from simpler starting materials. The key steps involve microwave-assisted intramolecular cascade double heck cyclization to access the ABCE ring of opium alkaloids with the required stereocenters in one pot. A photoinduced intramolecular hydroamination of carboxamide forms the D ring and completes the pentacyclic core of the morphinans. Following that, an oxidation followed by global reduction leads to the formation of (-)-codeine. Our synthesis relies on simple and classical reactions to address the opium alkaloids and will serve as an efficient route to access the other morphinans.

摘要

可待因和吗啡是少数几种直接用作药物治疗的天然产物之一。然而,这些天然产物的可用性在很大程度上依赖于自然资源。在此,我们报告了一种从更简单的起始原料出发,高效对映选择性地合成(-)-可待因的七步合成方法。关键步骤包括微波辅助的分子内级联双 Heck 环化,一锅法以所需的立体中心获得鸦片生物碱的 ABCE 环。酰胺的光诱导分子内氢胺化形成 D 环并完成吗啡喃的五环核心。之后,氧化后再进行整体还原,形成(-)-可待因。我们的合成依赖于简单而经典的反应来处理鸦片生物碱,将成为一种有效的方法来获得其他吗啡喃。

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