An Enantioselective Approach to Heteroatom-Containing Bicyclic Derivatives via Inverse-Electron-Demand Diels-Alder Reactions

被引：10
作者：
He, Jun-Xiong [1 ]
Si, Xu-Ge [1 ]
Lu, Qi-Tao [1 ]
Zhang, Qian-Wei [1 ]
Cai, Quan [1 ]
机构：
[1] Fudan Univ, Res Ctr Mol Recognit & Synth, Dept Chem, 220 Handan Rd, Shanghai 200433, Peoples R China
来源：
CHINESE JOURNAL OF CHEMISTRY | 2023年 / 41卷 / 01期
基金：
中国国家自然科学基金;
关键词：
Asymmetric catalysis; Heterocycles; Total synthesis; 2-Pyrones; Inverse-electron-demand Diels-Alder reaction; Cycloaddition; ASYMMETRIC TOTAL SYNTHESES; CONJUGATE ADDITION; ALKALOIDS; CYCLIZATION; CYCLOADDITIONS; VINBLASTINE; COMPLEXITY; CHEMISTRY; ANALOGS; BIOLOGY;
D O I：
10.1002/cjoc.202200441
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Comprehensive Summary Chiral heteroatom-containing bicyclic scaffolds are important pharmacophores and prevalent in bioactive natural products and drug molecules. Herein, we report a unified approach for the divergent synthesis of chiral heteroatom-containing bicyclic derivatives by lanthanide (III)-catalyzed asymmetric inverse-electron-demand Diels-Alder reactions of 2-pyrones. These reactions occur with various readily available dihydropyrroles and dihydrofurans as dienophiles, providing a step-economical synthetic platform for densely functionalized cis-hydroindoles and cis-hydrobenzofurans with excellent yields and enantioselectivities. The synthetic utility of this approach is demonstrated by the concise synthesis of (-)-alpha-lycorane and (-)-lycorine alkaloids.
引用
收藏
页码：21 / 26
页数：6
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