Accessing ladder-shape azetidine-fused indoline pentacycles through intermolecular regiodivergent aza-Paternò–Büchi reactions

Jianjian Huang, Tai-Ping Zhou, Ningning Sun, Huaibin Yu, Xixiang Yu, Rong-Zhen Liao (), Weijun Yao, Zhifeng Dai, Guojiao Wu and Fangrui Zhong ()
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Jianjian Huang: Huazhong University of Science and Technology (HUST)
Tai-Ping Zhou: Huazhong University of Science and Technology (HUST)
Ningning Sun: Huazhong University of Science and Technology (HUST)
Huaibin Yu: Zhengzhou Research Institute, Harbin Institute of Technology
Xixiang Yu: Huazhong University of Science and Technology (HUST)
Rong-Zhen Liao: Huazhong University of Science and Technology (HUST)
Weijun Yao: Zhejiang Sci-Tech University
Zhifeng Dai: Zhejiang Sci-Tech University
Guojiao Wu: Huazhong University of Science and Technology (HUST)
Fangrui Zhong: Huazhong University of Science and Technology (HUST)

Nature Communications, 2024, vol. 15, issue 1, 1-11

Abstract: Abstract Small molecules with conformationally rigid, three-dimensional geometry are highly desirable in drug development, toward which a direct, simple-to-complexity synthetic logic is still of considerable challenges. Here, we report intermolecular aza-[2 + 2] photocycloaddition (the aza-Paternò–Büchi reaction) of indole that facilely assembles planar building blocks into ladder-shape azetidine-fused indoline pentacycles with contiguous quaternary carbons, divergent head-to-head/head-to-tail regioselectivity, and absolute exo stereoselectivity. These products exhibit marked three-dimensionality, many of which possess 3D score values distributed in the highest 0.5% region with reference to structures from DrugBank database. Mechanistic studies elucidated the origin of the observed regio- and stereoselectivities, which arise from distortion-controlled C-N coupling scenarios. This study expands the synthetic repertoire of energy transfer catalysis for accessing structurally intriguing architectures with high molecular complexity and underexplored topological chemical space.

Date: 2024
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DOI: 10.1038/s41467-024-45687-0

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