Efficient Synthesis of (-)-Corynoline by Enantioselective Palladium-Catalyzed α-Arylation with Sterically Hindered Substrates

被引：52

作者：

Rao, Xiaofeng ^{[1
]}

Li, Naikai ^{[1
]}

Bai, Heng ^{[1
]}

Dai, Chaodi ^{[1
]}

Wang, Zheng ^{[2
]}

Tang, Wenjun ^{[1
]}

机构：

[1] Univ Chinese Acad Sci, Shanghai Inst Organ Chem, Ctr Excellence Mol Synth, State Key Lab Bioorgan & Nat Prod Chem, 345 Ling Ling Rd, Shanghai 200032, Peoples R China

[2] Astra Zeneca China, Informat & Technol, Shanghai, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 38期

关键词：

arylation; corynoline; enantioselectivity; palladium catalysis; phosphine ligands; MIYAURA COUPLING REACTIONS; CARBON QUATERNARY CENTERS; SCELETIUM ALKALOIDS; CORYDALIS-INCISA; NATURAL-PRODUCTS; DEAROMATIVE CYCLIZATION; ABSOLUTE-CONFIGURATION; FORMAL SYNTHESIS; AERIAL PARTS; CONSTRUCTION;

D O I：

10.1002/anie.201807302

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Sterically hindered substrates can be employed in an enantioselective palladium-catalyzed alpha-arylation with the chiral monophosphorus ligand BI-DIME. This process enabled an efficient synthesis of the antidepressant (S)-nafenodone, a four-step enantioselective synthesis of the Sceletium alkaloid (+)-sceletium A-4, a concise five-step enantioselective synthesis of (-)-corynoline, as well as a three-step preparation of (-)-DeN-corynoline.

引用

页码：12328 / 12332

页数：5

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