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Peer-reviewedCC BY-NC-NDNature communications

Practical synthesis of 3-Oxa/Aza-bicyclo[3.1.1]heptanes from 3-Oxa/Aza[3.1.1]propellanes.

  • Qin Jiang1
  • Jianyang Dong2
  • Fang Lei1
  • Yanfeng Han1
  • Mingxin Li1
  • Yilin Zhang1
  • Juan Fan1
  • Huaming Sun1
  • Ting Li1
  • Shuoyi Chen1
  • Zhendan Chen1
  • Dong Xue3
  1. 1Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, China.
  2. 2Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, China. [email protected].
  3. 3Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, China. [email protected].
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Abstract

While bicyclo[1.1.1]pentanes (BCPs) and bicyclo[3.1.1]heptanes (BCHeps) serve as established 3D bioisosteres for para- and meta-substituted benzenes, accessible via ring-opening of their corresponding propellanes, the integration of heteroatoms into these propellane scaffolds has remained elusive. Herein, we report the practical synthesis of 3-oxa/aza[3.1.1]propellanes, two heteroatom-containing analogues of propellane, from 1,5-diiodo-3-hetero-BCHeps. On this basis, radical-based transformations of 3-oxa/aza[3.1.1]propellane are established, enabling efficient and divergent access to a broad range of bridgehead-disubstituted 3-oxa/aza-BCHep derivatives as saturated isosteres of meta-substituted benzenes. Furthermore, representative 3-oxa-BCHep derivatives are converted into functionalized synthetic building blocks; this scaffold is also introduced into the antiepileptic drug URB597 and anticancer drug sonidegib. These results demonstrate that the 3-oxa/aza[3.1.1] frameworks provide a general and feasible synthetic platform for the construction of heteroatom-containing cage-like bioisosteres and the optimization of drug properties.

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Cite

BibTeXRIS
BibTeX
@article{jiang2026practical,
  title = {{Practical synthesis of 3-Oxa/Aza-bicyclo[3.1.1]heptanes from 3-Oxa/Aza[3.1.1]propellanes.}},
  author = {Qin Jiang and Jianyang Dong and Fang Lei and Yanfeng Han and Mingxin Li and Yilin Zhang and Juan Fan and Huaming Sun and Ting Li and Shuoyi Chen and Zhendan Chen and Dong Xue},
  journal = {Nature communications},
  year = {2026},
  month = sep,
  doi = {10.1038/s41467-026-76235-7},
  url = {https://europepmc.org/article/MED/42893976},
  note = {CC BY-NC-ND},
}
RIS
TY  - JOUR
TI  - Practical synthesis of 3-Oxa/Aza-bicyclo[3.1.1]heptanes from 3-Oxa/Aza[3.1.1]propellanes.
AU  - Qin Jiang
AU  - Jianyang Dong
AU  - Fang Lei
AU  - Yanfeng Han
AU  - Mingxin Li
AU  - Yilin Zhang
AU  - Juan Fan
AU  - Huaming Sun
AU  - Ting Li
AU  - Shuoyi Chen
AU  - Zhendan Chen
AU  - Dong Xue
PY  - 2026
DA  - 2026/09/16
JO  - Nature communications
DO  - 10.1038/s41467-026-76235-7
UR  - https://europepmc.org/article/MED/42893976
AB  - While bicyclo[1.1.1]pentanes (BCPs) and bicyclo[3.1.1]heptanes (BCHeps) serve as established 3D bioisosteres for para- and meta-substituted benzenes, accessible via ring-opening of their corresponding propellanes, the integration of heteroatoms into these propellane scaffolds has remained elusive. Herein, we report the practical synthesis of 3-oxa/aza[3.1.1]propellanes, two heteroatom-containing analogues of propellane, from 1,5-diiodo-3-hetero-BCHeps. On this basis, radical-based transformations of 3-oxa/aza[3.1.1]propellane are established, enabling efficient and divergent access to a broad range of bridgehead-disubstituted 3-oxa/aza-BCHep derivatives as saturated isosteres of meta-substituted benzenes. Furthermore, representative 3-oxa-BCHep derivatives are converted into functionalized synthetic building blocks; this scaffold is also introduced into the antiepileptic drug URB597 and anticancer drug sonidegib. These results demonstrate that the 3-oxa/aza[3.1.1] frameworks provide a general and feasible synthetic platform for the construction of heteroatom-containing cage-like bioisosteres and the optimization of drug properties.
SN  - 2041-1723
ER  -