{
  "abstract": "We report the enantioselective formal synthesis of neoxaline, an archetypal member of the oxaline alkaloids. An initial approach employs an asymmetric deaminative cross-coupling to install the 1,1-dimethylallyl (\"reverse prenyl\") moiety onto an oxindole framework. Subsequent strategies employ iridium-catalyzed reverse prenylation onto tryptamine scaffolds, enabling the facile construction of a densely functionalized α-carboline framework. The route detailed herein represents a potentially general strategy for the synthesis of related oxaline alkaloids.",
  "abstract_shown": true,
  "affiliations": [
    "The Warren and Katharine Schlinger Laboratory for Chemistry and Chemical Engineering, Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California91125, United States."
  ],
  "article_type": "research article",
  "arxiv": null,
  "author_total": 2,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Jonathan Farhi"
    },
    {
      "affs": [
        0
      ],
      "name": "Brian M Stoltz",
      "orcid": "0000-0001-9837-1528"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/84xhydp0na3rv.bib",
  "cited_by": 0,
  "doi": "10.1021/acs.joc.6c02094",
  "fulltext_url": "https://europepmc.org/articles/PMC13682208",
  "id": "84xhydp0na3rv",
  "issns": [
    "0022-3263",
    "1520-6904"
  ],
  "landing_url": "https://europepmc.org/article/MED/42917571",
  "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|Asymmetric Synthesis and Catalysis"
    ]
  ],
  "openalex": "W7214739089",
  "pdf_url": "https://europepmc.org/articles/PMC13682208?pdf=render",
  "pmcid": "PMC13682208",
  "pmid": "42917571",
  "published": "2026-10-01",
  "publisher": null,
  "ris": "https://research.draconitic.com/paper/84xhydp0na3rv.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:20:36Z",
      "native_id": "MED:42917571",
      "source": "europepmc",
      "url": "https://europepmc.org/article/MED/42917571"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Asymmetric Synthesis and Catalysis",
      "subfield": "organic"
    }
  ],
  "title": "Enantioselective Formal Synthesis of (-)-Neoxaline Enabled by an Asymmetric Ir-Catalyzed Reverse Prenylation.",
  "title_text": "Enantioselective Formal Synthesis of (-)-Neoxaline Enabled by an Asymmetric Ir-Catalyzed Reverse Prenylation.",
  "type": "peer-reviewed",
  "updated_at": "2026-10-30T12:20:36Z",
  "url": "https://research.draconitic.com/paper/84xhydp0na3rv",
  "venue": "The Journal of organic chemistry",
  "versions": []
}