A modular and divergent approach for the total synthesis of Elaeocarpus alkaloids,Organic Chemistry Frontiers

当前位置： X-MOL 学术 › Org. Chem. Front. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

A modular and divergent approach for the total synthesis of Elaeocarpus alkaloids
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2022-11-08 , DOI: 10.1039/d2qo01460b
Guang Tian _{1,

2} , Yi-Chi Zhang ₂ , Chuanguang Qin ₁ , Jie Wang _{2,

3}

Affiliation

Herein we report a unified strategy for the divergent total synthesis of six Elaeocarpus alkaloids in 6–10 steps from commercially available materials. This modular approach relied on the rapid construction of the tetrahydrobenzopyran-4-one framework through an aldol/dehydration/oxa-Michael process to set all carbons and functional groups ready for the core construction. A key NbCl₅-mediated intramolecular Mannich reaction was used to build the C ring and secure both stereoisomers existing in these natural products. Finally, a diversification was achieved through the intermediacy of thioamide, with the side chain of elaeocarfoline A/B installed by an Eschenmoser sulfide contraction/reduction sequence.

中文翻译：

一种用于合叶树生物碱全合成的模块化和发散方法

在此，我们报告了一种统一的策略，用于从市售材料分 6-10 步分步全合成六种杜鹃花生物碱。这种模块化方法依赖于通过羟醛/脱水/氧杂-迈克尔过程快速构建四氢苯并吡喃-4-酮框架，为核心构建准备好所有碳和官能团。关键的 NbCl ₅介导的分子内曼尼希反应用于构建 C 环并确保这些天然产物中存在的两种立体异构体。最后，通过硫代酰胺的中介作用实现了多样化，其中 elaeocarfoline A/B 的侧链由 Eschenmoser 硫化物收缩/还原序列安装。

更新日期：2022-11-08

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11