Ten-Step Total Synthesis of (−)-Andranginine

The total synthesis of the indole alkaloid (−)-andranginine 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 reac...

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Bibliographic Details
Published in:Organic letters 2022-09, Vol.24 (37), p.6880-6883
Main Authors: Zhao, Yulong, Li, Jiaxin, Ma, Ruize, He, Feifei, Shi, Hongliang, Duan, Xiaoguang, Li, Huilin, Xie, Xingang, She, Xuegong
Format: Article
Language:English
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Summary:The total synthesis of the indole alkaloid (−)-andranginine 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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02927