Ten-Step Total Synthesis of (-)-Andranginine

被引:1
|
作者
Zhao, Yulong [1 ]
Li, Jiaxin [1 ]
Ma, Ruize [1 ]
He, Feifei [1 ]
Shi, Hongliang [1 ]
Duan, Xiaoguang [1 ]
Li, Huilin [1 ]
Xie, Xingang [1 ]
She, Xuegong [1 ]
机构
[1] Lanzhou Univ, Coll Chem & Chem Engn, State Key Lab Appl Organ Chem, Lanzhou 730000, Gansu, Peoples R China
基金
美国国家科学基金会;
关键词
INDOLE ALKALOIDS; ASYMMETRIC-SYNTHESIS; ANDRANGININE; MELODINUS;
D O I
10.1021/acs.orglett.2c02927
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The total synthesis of the indole alkaloid (-)-an-dranginine has been achieved in 10 steps. Key reactions of the synthesis include a nucleophilic addition of acetylenyl anion to chiral N-sulfinyl imine, an intramolecular N-alkylation reaction to close the C ring, and a dienyne metathesis cascade reaction to construct the DE rings. Meanwhile, 16-epi-(-)-andranginine was also obtained with the developed strategy.
引用
收藏
页码:6880 / 6883
页数:4
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