Radical-Cation Cascade to Aryltetralin Cyclic Ether Lignans Under Visible-Light Photoredox Catalysis

被引:22
|
作者
Xiang, Jia-Chen [1 ]
Wang, Qian [1 ]
Zhu, Jieping [1 ]
机构
[1] Ecole Polytech Fed Lausanne, Inst Chem Sci & Engn, Lab Synth & Nat Prod, SB,ISIC,BCH 5304, CH-1015 Lausanne, Switzerland
基金
瑞士国家科学基金会;
关键词
cycloaddition; lignans; natural products; organocatalysis; radicals; ELECTRON-TRANSFER REACTIONS; INTERMOLECULAR 2+2 CYCLOADDITION; DIELS-ALDER REACTIONS; PODOPHYLLOTOXIN; DIMERIZATION; REGIOSELECTIVITY; PHOTOCATALYSIS; STYRENES; DIOXYGEN; ALKENES;
D O I
10.1002/anie.202007548
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The development of concise, sustainable, and cost-effective synthesis of aryltetralin lignans, bearing either a fused lactone or cyclic ether, is of significant medicinal importance. Reported is that in the presence of Fukuzumi's acridinium salt under blue LED irradiation, functionalized dicinnamyl ether derivatives are converted into aryltetralin cyclic ether lignans with concurrent generation of three stereocenters in good to high yields with up to 20:1 diastereoselectivity. Oxidation of an alkene to the radical cation is key to the success of this formal Diels-Alder reaction of electronically mismatched diene and dienophile. Applying this methodology, six natural products, aglacin B, aglacin C, sulabiroin A, sulabiroin B, gaultherin C, and isoshonanin, are synthesized in only two to three steps from readily available biomass-derived monolignols. A revised structure is proposed for gaultherin C.
引用
收藏
页码:21195 / 21202
页数:8
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