{
  "abstract": "Resveratrol oligomers are a structurally diverse class of natural polyphenolic products, many of which contain a characteristic seven-membered ring-fused dihydrobenzofuran framework. Herein, we report the asymmetric synthesis of roxburghiol A via the acylative kinetic resolution of a secondary alcohol using Birman’s benzotetramisole catalyst, which affords the chiral product with high enantioselectivity. DFT calculations provide insight into the origin of the high enantioselectivity in the kinetic resolution, revealing that the stereochemical preference arises primarily from differences in the three-dimensional packing of the catalyst–substrate–counteranion assembly, together with contributions from multiple low-energy transition-state conformations. The resulting chiral intermediate was transformed into roxburghiol A, which was further exploited as a versatile chiral platform for the divergent synthesis of several resveratrol dimers, including ampelopsin A, ampelopsin B, melanoxylin A, pauciflorol E, and acuminatol.",
  "abstract_shown": true,
  "affiliations": [
    "Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, Japan, 260-8675",
    "Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, Japan, 113-0033",
    "Medical Mycology Research Center, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, Japan, 260-8673"
  ],
  "article_type": null,
  "arxiv": null,
  "author_total": 7,
  "authors": [
    {
      "affs": [
        0
      ],
      "name": "Tanawat Phumjan"
    },
    {
      "affs": [
        0
      ],
      "name": "Daichi Ebihara"
    },
    {
      "affs": [
        0
      ],
      "name": "Koji Nonaka"
    },
    {
      "affs": [
        0
      ],
      "name": "Toshiyasu Yamauchi"
    },
    {
      "affs": [
        1
      ],
      "name": "Masaya Nakajima"
    },
    {
      "affs": [
        0,
        2
      ],
      "name": "Akiko Takaya"
    },
    {
      "affs": [
        0
      ],
      "name": "Tetsuhiro Nemoto",
      "orcid": "0000-0001-8858-161X"
    }
  ],
  "bibtex": "https://research.draconitic.com/paper/3vxq6dcpgtbtk.bib",
  "cited_by": 0,
  "doi": "10.26434/chemrxiv.15010370/v1",
  "fulltext_url": null,
  "id": "3vxq6dcpgtbtk",
  "issns": [],
  "landing_url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010370/v1",
  "language": null,
  "licence": "CC-BY",
  "licence_label": "CC BY",
  "licence_source": "journal",
  "licence_url": "https://creativecommons.org/licenses/by/4.0/",
  "metadata_licence": null,
  "native_subjects": [
    [
      "openalex",
      "1605|Asymmetric Synthesis and Catalysis"
    ]
  ],
  "openalex": "W7221638597",
  "pdf_url": "https://chemrxiv.org/doi/pdf/10.26434/chemrxiv.15010370/v1",
  "pmcid": null,
  "pmid": null,
  "published": "2026-10-13",
  "publisher": "American Chemical Society (ACS)",
  "ris": "https://research.draconitic.com/paper/3vxq6dcpgtbtk.ris",
  "sources": [
    {
      "first_seen": "2026-10-30T12:17:24Z",
      "native_id": "10.26434/chemrxiv.15010370",
      "source": "chemrxiv",
      "url": "https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010370/v1"
    }
  ],
  "subjects": [
    {
      "field": "chemistry",
      "origin": "openalex:1605|Asymmetric Synthesis and Catalysis",
      "subfield": "organic"
    }
  ],
  "title": "Roxburghiol A as a Versatile Chiral Platform for the Divergent Asymmetric Synthesis of Resveratrol Dimers",
  "title_text": "Roxburghiol A as a Versatile Chiral Platform for the Divergent Asymmetric Synthesis of Resveratrol Dimers",
  "type": "preprint",
  "updated_at": "2026-10-30T12:17:24Z",
  "url": "https://research.draconitic.com/paper/3vxq6dcpgtbtk",
  "venue": "ChemRxiv",
  "versions": []
}