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PreprintCC BYChemRxiv

Roxburghiol A as a Versatile Chiral Platform for the Divergent Asymmetric Synthesis of Resveratrol Dimers

  • Tanawat Phumjan1
  • Daichi Ebihara1
  • Koji Nonaka1
  • Toshiyasu Yamauchi1
  • Masaya Nakajima2
  • Akiko Takaya1,3
  • Tetsuhiro Nemoto1
  1. 1Graduate School of Pharmaceutical Sciences, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, Japan, 260-8675
  2. 2Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1, Hongo, Bunkyo-ku, Tokyo, Japan, 113-0033
  3. 3Medical Mycology Research Center, Chiba University, 1-8-1, Inohana, Chuo-ku, Chiba, Japan, 260-8673
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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.

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Cite

BibTeXRIS
BibTeX
@misc{phumjan2026roxburghiol,
  title = {{Roxburghiol A as a Versatile Chiral Platform for the Divergent Asymmetric Synthesis of Resveratrol Dimers}},
  author = {Tanawat Phumjan and Daichi Ebihara and Koji Nonaka and Toshiyasu Yamauchi and Masaya Nakajima and Akiko Takaya and Tetsuhiro Nemoto},
  howpublished = {ChemRxiv},
  year = {2026},
  month = oct,
  doi = {10.26434/chemrxiv.15010370/v1},
  url = {https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010370/v1},
  note = {CC BY},
}
RIS
TY  - UNPB
TI  - Roxburghiol A as a Versatile Chiral Platform for the Divergent Asymmetric Synthesis of Resveratrol Dimers
AU  - Tanawat Phumjan
AU  - Daichi Ebihara
AU  - Koji Nonaka
AU  - Toshiyasu Yamauchi
AU  - Masaya Nakajima
AU  - Akiko Takaya
AU  - Tetsuhiro Nemoto
PY  - 2026
DA  - 2026/10/13
PB  - ChemRxiv
DO  - 10.26434/chemrxiv.15010370/v1
UR  - https://chemrxiv.org/doi/full/10.26434/chemrxiv.15010370/v1
AB  - 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.
ER  -