{
  "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.",
  "abstract_shown": true,
  "affiliations": [
    "Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, China.",
    "Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, China. jydong@snnu.edu.cn.",
    "Key Laboratory of Applied Surface and Colloid Chemistry, Ministry of Education, and School of Chemistry and Chemical Engineering, Shaanxi Normal University, Xi'an, China. xuedong_welcome@snnu.edu.cn."
  ],
  "article_type": "research article",
  "arxiv": null,
  "author_total": 12,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Qin Jiang"
    },
    {
      "affs": [
        1
      ],
      "name": "Jianyang Dong",
      "orcid": "0000-0002-7070-0251"
    },
    {
      "affs": [
        0
      ],
      "name": "Fang Lei"
    },
    {
      "affs": [
        0
      ],
      "name": "Yanfeng Han"
    },
    {
      "affs": [
        0
      ],
      "name": "Mingxin Li"
    },
    {
      "affs": [
        0
      ],
      "name": "Yilin Zhang"
    },
    {
      "affs": [
        0
      ],
      "name": "Juan Fan"
    },
    {
      "affs": [
        0
      ],
      "name": "Huaming Sun",
      "orcid": "0000-0001-7133-1948"
    },
    {
      "affs": [
        0
      ],
      "name": "Ting Li"
    },
    {
      "affs": [
        0
      ],
      "name": "Shuoyi Chen"
    },
    {
      "affs": [
        0
      ],
      "name": "Zhendan Chen"
    },
    {
      "affs": [
        2
      ],
      "name": "Dong Xue",
      "orcid": "0000-0002-7269-6356"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/cfyk0cmdyjzks.bib",
  "cited_by": 0,
  "doi": "10.1038/s41467-026-76235-7",
  "fulltext_url": "https://europepmc.org/articles/PMC13677720",
  "id": "cfyk0cmdyjzks",
  "issns": [
    "2041-1723"
  ],
  "landing_url": "https://europepmc.org/article/MED/42893976",
  "language": "eng",
  "licence": "CC-BY-NC-ND",
  "licence_label": "CC BY-NC-ND",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by-nc-nd/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Cyclopropane Reaction Mechanisms"
    ]
  ],
  "openalex": "W7213247264",
  "pdf_url": "https://europepmc.org/articles/PMC13677720?pdf=render",
  "pmcid": "PMC13677720",
  "pmid": "42893976",
  "published": "2026-09-16",
  "publisher": null,
  "ris": "https://research.draconitic.com/paper/cfyk0cmdyjzks.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:19:41Z",
      "native_id": "MED:42893976",
      "source": "europepmc",
      "url": "https://europepmc.org/article/MED/42893976"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Cyclopropane Reaction Mechanisms",
      "subfield": "organic"
    }
  ],
  "title": "Practical synthesis of 3-Oxa/Aza-bicyclo[3.1.1]heptanes from 3-Oxa/Aza[3.1.1]propellanes.",
  "title_text": "Practical synthesis of 3-Oxa/Aza-bicyclo[3.1.1]heptanes from 3-Oxa/Aza[3.1.1]propellanes.",
  "type": "peer-reviewed",
  "updated_at": "2026-10-30T12:19:41Z",
  "url": "https://research.draconitic.com/paper/cfyk0cmdyjzks",
  "venue": "Nature communications",
  "versions": []
}