Catalytic enantioselective nitrone cycloadditions enabling collective syntheses of indole alkaloids

Tetrahydro-β-carboline skeletons are prominent and ubiquitous in an extraordinary range of indole alkaloid natural products and pharmaceutical compounds. Powerful synthetic approaches for stereoselective synthesis of tetrahydro-β-carboline skeletons have immense impacts and have attracted enormous a...

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Bibliographic Details
Published in:Nature communications 2024-07, Vol.15 (1), p.6429-15, Article 6429
Main Authors: Tian, Xiaochen, Xuan, Tengfei, Gao, Jingkun, Zhang, Xinyu, Liu, Tao, Luo, Fengbiao, Pang, Ruochen, Shao, Pengcheng, Yang, Yun-Fang, Wang, Yang
Format: Article
Language:English
Subjects:
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Alkaloids
Asymmetry
Chemical synthesis
Cycloaddition
Enantiomers
Green chemistry
Humanities and Social Sciences
Indoles
Methods
multidisciplinary
Natural products
Pharmaceuticals
Phosphoric acid
Science
Science (multidisciplinary)
Stereochemistry
Stereoselectivity
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Summary:Tetrahydro-β-carboline skeletons are prominent and ubiquitous in an extraordinary range of indole alkaloid natural products and pharmaceutical compounds. Powerful synthetic approaches for stereoselective synthesis of tetrahydro-β-carboline skeletons have immense impacts and have attracted enormous attention. Here, we outline a general chiral phosphoric acid catalyzed asymmetric 1,3-dipolar cycloaddition of 3,4-dihydro-β-carboline-2-oxide type nitrone that enables access to three types of chiral tetrahydro-β-carbolines bearing continuous multi-chiral centers and quaternary chiral centers. The method displays different endo/exo selectivity from traditional nitrone chemistry. The distinct power of this strategy has been illustrated by application to collective and enantiodivergent total syntheses of 40 tetrahydro-β-carboline-type indole alkaloid natural products with divergent stereochemistry and varied architectures. Stereoselective synthesis of tetrahydro-βcarboline skeletons have immense impacts and attract enormous attention. Here, the authors report chiral phosphoric acid catalyzed asymmetric 1,3-dipolar cycloaddition, affording three types of chiral tetrahydro-β-carbolines bearing continuous multi-chiral centers and quaternary chiral centers.
ISSN:2041-1723
2041-1723
DOI:10.1038/s41467-024-50509-4