{
  "abstract": "Studies toward spiroetherone A uncovered an unexpectedly rich reactivity landscape within the avarane skeleton. An intramolecular Michael addition onto a quinone enabled access to the characteristic spiroenedione core of the natural product. Alongside this transformation, diverse and unanticipated reaction pathways emerged, generating structurally complex molecular architectures. These included an unusual S N Ar on an electron-rich arene, a McMurry-type ketone-ester coupling with concomitant reductive deoxygenation, or Wagner-Meerwein rearrangements furnishing oxaspiro[4.5]dienone and dihydrochromane scaffolds. As other divergent transformations developed, a (3 + 2) quinone monoacetal dimerization produced a dibenzofuran motif close to popolohuanone E, whereas a PIDA-mediated alkene-phenol nitrile cyclization/Ritter reaction sequence delivered an unprecedented pentacyclic bridged imidate. This work demonstrates how synthetic exploration toward complex natural products can reveal unforeseen modes of reactivity and skeletal diversification.",
  "abstract_shown": true,
  "affiliations": [],
  "article_type": null,
  "arxiv": null,
  "author_total": 4,
  "authors": [
    {
      "name": "Guillaume Schoenn"
    },
    {
      "name": "Régis Guillot"
    },
    {
      "name": "Cyrille Kouklovsky"
    },
    {
      "name": "Guillaume Vincent"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/b4qrbtwkexrm3.bib",
  "cited_by": 0,
  "doi": "10.1002/ceur.70350",
  "fulltext_url": null,
  "id": "b4qrbtwkexrm3",
  "issns": [
    "2751-4765"
  ],
  "landing_url": "https://hal.science/hal-05770600v1",
  "language": "en",
  "licence": "CC-BY-NC-SA-4.0",
  "licence_label": "CC BY-NC-SA 4.0",
  "licence_source": "article",
  "licence_url": "https://creativecommons.org/licenses/by-nc-sa/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "hal",
      "0.chim"
    ],
    [
      "openalex",
      "1605|Organic Chemistry Synthesis Methods"
    ]
  ],
  "openalex": "W7204493506",
  "pdf_url": "https://hal.science/hal-05770600/document",
  "pmcid": null,
  "pmid": null,
  "published": "2026-08-27",
  "publisher": "Wiley",
  "ris": "https://research.draconitic.com/paper/b4qrbtwkexrm3.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:43Z",
      "native_id": "hal-05770600",
      "source": "hal",
      "url": "https://hal.science/hal-05770600v1"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Organic Chemistry Synthesis Methods",
      "subfield": "organic"
    }
  ],
  "title": "Diversification of the Avarane Skeleton Toward Spiroetherone A",
  "title_text": "Diversification of the Avarane Skeleton Toward Spiroetherone A",
  "type": "peer-reviewed",
  "updated_at": "2026-10-30T12:17:43Z",
  "url": "https://research.draconitic.com/paper/b4qrbtwkexrm3",
  "venue": "ChemistryEurope",
  "versions": []
}