Catalytic Diastereoselective Synthesis of Bicyclo[3.2.1]octanediones

The bicyclo[3.2.1]octanone and bicyclo[3.2.1]octanedione scaffolds, along with their derivatives, are ubiquitous in natural products and synthetic pharmaceuticals. However, the synthetic routes to access these scaffolds have been relatively underdeveloped. Herein, this study introduces a unique reaction between pent‐4‐ene‐1,3‐diones and vinyl diketones, which serves as a versatile platform for the efficient synthesis of a wide array of bicyclo[3.2.1]octanediones in good to excellent yields. Furthermore, this study method facilitates diverse downstream transformations of these products, underscoring the versatility and potential of diketone‐based chemistry in constructing complex molecules.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2025-06-16
DOI
https://doi.org/10.1002/adsc.202500324
Primary Topic
Axial and Atropisomeric Chirality Synthesis
Type
article
Field-Weighted Citation Impact
0.00

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article

Catalytic Diastereoselective Synthesis of Bicyclo[3.2.1]octanediones

Shouang Lan, Xinqiang Fang, Lili Zhao, Wennan Dong et al.
Advanced Synthesis & Catalysis
Axial and Atropisomeric Chirality Synthesis
article

Catalytic Diastereoselective Synthesis of Bicyclo[3.2.1]octanediones

Shouang Lan, Xinqiang Fang, Lili Zhao, Wennan Dong, Chao Xu, S. L. Yang, Liyuan Zhou, Chunyun Jiang, Qinqin Cui, Bao‐Tian Luo, Xiangwen Kong, Caiyi Ren
article en

Abstract

The bicyclo[3.2.1]octanone and bicyclo[3.2.1]octanedione scaffolds, along with their derivatives, are ubiquitous in natural products and synthetic pharmaceuticals. However, the synthetic routes to access these scaffolds have been relatively underdeveloped. Herein, this study introduces a unique reaction between pent‐4‐ene‐1,3‐diones and vinyl diketones, which serves as a versatile platform for the efficient synthesis of a wide array of bicyclo[3.2.1]octanediones in good to excellent yields. Furthermore, this study method facilitates diverse downstream transformations of these products, underscoring the versatility and potential of diketone‐based chemistry in constructing complex molecules.

Advanced Synthesis & CatalysisVol. 367(13)
Fujian Normal University (CN), Fujian Institute of Research on the Structure of Matter (CN), Jining University (CN), Pingxiang University (CN), University of Chinese Academy of Sciences (CN)
National Natural Science Foundation of China, Chinese Academy of Sciences, Natural Science Foundation of Fujian Province, Natural Science Foundation of Shandong Province
Openalex Percentile: Top 89%
Axial and Atropisomeric Chirality Synthesis
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Catalytic Diastereoselective Synthesis of Bicyclo[3.2.1]octanediones — Shouang Lan, Xinqiang Fang, et al. · Advanced Synthesis & Catalysis (2025) | TGRS Research Map | TGRS