Catalytic enantioselective nitrone cycloadditions enabling collective syntheses of indole alkaloids

Xiaochen Tian, Tengfei Xuan, Jingkun Gao, Xinyu Zhang, Tao Liu, Fengbiao Luo, Ruochen Pang, Pengcheng Shao, Yun-Fang Yang () and Yang Wang ()
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Xiaochen Tian: Ocean University of China
Tengfei Xuan: Ocean University of China
Jingkun Gao: Zhejiang University of Technology
Xinyu Zhang: Ocean University of China
Tao Liu: Ocean University of China
Fengbiao Luo: Ocean University of China
Ruochen Pang: Ocean University of China
Pengcheng Shao: Ocean University of China
Yun-Fang Yang: Zhejiang University of Technology
Yang Wang: Ocean University of China

Nature Communications, 2024, vol. 15, issue 1, 1-15

Abstract: Abstract 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.

Date: 2024
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DOI: 10.1038/s41467-024-50509-4

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