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
收藏
页码：12328 / 12332
页数：5
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