Total synthesis of sinopyrine B

The first total synthesis of sinopyrine B has been concisely achieved in 10 linear steps with a 7% overall yield. Importantly, the crucial pyrrolo[2,1-a]isoquinoline skeleton, widely existing in various natural products and pharmacological molecules, was rapidly constructed in one step through a uni...

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Bibliographic Details
Published inTetrahedron letters Vol. 106; pp. 154072 - 154075
Main Authors Li, Jing, Jiang, Li-Ming, Cheng, Fu, Zhou, Yu-Jia, Duan, Dong-Sen, Zhu, Dao-Yong, Zhang, Kun, Xiong, Zhuang, Wang, Shao-Hua
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.09.2022
Elsevier
Subjects
[3+2] cyclization
Chemistry
Chemistry, Organic
Natural product
Physical Sciences
Science & Technology
Sinopyrine B
Total Synthesis
Total Synthesis
[3+2] cyclization
Natural product
Sinopyrine B
CORE
TRIMETHYL ETHER
1ST SYNTHESIS
LAMELLARIN ALKALOIDS ISOLATION
NINGALIN
LUKIANOL
PYRROLES
DISCOVERY
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Summary:The first total synthesis of sinopyrine B has been concisely achieved in 10 linear steps with a 7% overall yield. Importantly, the crucial pyrrolo[2,1-a]isoquinoline skeleton, widely existing in various natural products and pharmacological molecules, was rapidly constructed in one step through a unique formal [3 + 2] cyclization between 2-(3,4-dihydroisoquinolin-2(1H)-yl)malononitrile 3 and trimethyl silyl acetylene as the key step. [Display omitted] The first total synthesis of sinopyrine B has been concisely achieved in 10 linear steps with a 7 % overall yield. Importantly, the crucial pyrrolo[2,1-a]isoquinoline skeleton, widely existing in various natural products and pharmacological molecules, was rapidly constructed in one step through a unique formal [3 + 2] cyclization between 2-(3,4-dihydroisoquinolin-2(1H)-yl)malononitrile 3 and trimethyl silyl acetylene as the key step.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2022.154072