{
  "abstract": "An unexpected cyanide-mediated rearrangement of conjugated lactones is described, providing access to novel tricyclic furopyrrolidinones. This reaction occurs in a stoichiometry- and substrate-dependent manner, induced by multiple additions of cyanide to α,β,γ,δ-unsaturated lactones bearing suitable aryl substituents, providing products with adjacent ether, nitrile, and lactam functionalities. Single-crystal X-ray diffraction (SCXRD) studies of two products support the stereochemical assignments, providing evidence of a dynamic equilibrium process.",
  "abstract_shown": true,
  "affiliations": [
    "Department of Chemistry, University of Iowa, Iowa City, Iowa52242, United States."
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 2,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Ebuka L Onyeyilim",
      "orcid": "0000-0002-7854-8477"
    },
    {
      "affs": [
        0
      ],
      "name": "David B C Martin",
      "orcid": "0000-0002-8084-8225"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/7hetcekjxxhye.bib",
  "cited_by": 0,
  "doi": "10.1021/acs.joc.6c01880",
  "fulltext_url": "https://europepmc.org/articles/PMC13682204",
  "id": "7hetcekjxxhye",
  "issns": [
    "0022-3263",
    "1520-6904"
  ],
  "landing_url": "https://europepmc.org/article/MED/42917576",
  "language": "eng",
  "licence": "CC-BY",
  "licence_label": "CC BY",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Organic Chemistry Synthesis Methods"
    ]
  ],
  "openalex": "W7214903092",
  "pdf_url": "https://europepmc.org/articles/PMC13682204?pdf=render",
  "pmcid": "PMC13682204",
  "pmid": "42917576",
  "published": "2026-10-01",
  "publisher": null,
  "ris": "https://research.draconitic.com/paper/7hetcekjxxhye.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:20:36Z",
      "native_id": "MED:42917576",
      "source": "europepmc",
      "url": "https://europepmc.org/article/MED/42917576"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Organic Chemistry Synthesis Methods",
      "subfield": "organic"
    }
  ],
  "title": "Unexpected Rearrangement of Unsaturated Lactones to Give Tricyclic Furopyrrolidinones.",
  "title_text": "Unexpected Rearrangement of Unsaturated Lactones to Give Tricyclic Furopyrrolidinones.",
  "type": "peer-reviewed",
  "updated_at": "2026-10-30T12:20:36Z",
  "url": "https://research.draconitic.com/paper/7hetcekjxxhye",
  "venue": "The Journal of organic chemistry",
  "versions": []
}