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Peer-reviewedCC BYJournal of the American Chemical Society

Traversing the Regioselectivity of Intermolecular Pericyclic Aryne Reactions: Total Syntheses of Laetevirenol A and Isoampelopsin D.

  • Long Huu Nguyen1
  • Seoyeong Kim1
  • Jiah Kim1
  • EunHyeon Kim2
  • Sugyeong Ha1,3
  • Myeonggyo Jeong1,3
  • Ki Wung Chung1,3
  • Yeonjoon Kim2
  • Seokwoo Lee4
  • Hwayoung Yun1,3
4 affiliations
  1. 1College of Pharmacy, Pusan National University, Busan46241, Republic of Korea.
  2. 2Department of Chemistry, Pukyong National University, Busan48513, Republic of Korea.
  3. 3Research Institute for Drug Development, Pusan National University, Busan46241, Republic of Korea.
  4. 4College of Pharmacy, Chungnam National University, Daejeon34134, Republic of Korea.
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Abstract

Resveratrol-derived natural products feature a diverse group of stilbenoids, characterized by extensive structural variation and pharmacological potential. Herein, we document our innovation in the synthesis of laetevirenol A, a biologically captivating resveratrol dimer, and isoampelopsin D enabled by operating an aryne-based synthetic program. The synthetic strategy involves the incorporation of aryne building blocks into methylene indane/indene nuclei by harnessing their innate reactivity. A dehydro Diels-Alder cycloaddition and an aryne-ene reaction were developed to construct the carbon framework of laetevirenol A and isoampelopsin D. Attempts were made to rationalize the unexpected regioselectivity behavior of crucial benzyne reactions from both empirical and computational perspectives. Ultimately, laetevirenol A and its analogs were also biologically investigated to uncover their potential antioxidant activities. This work offers valuable insights into the regioselectivity of intermolecular pericyclic aryne reactions and serves as an example of controlling aryne regioselectivities in the synthesis of molecular targets.

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Cite

BibTeXRIS
BibTeX
@article{nguyen2026traversing,
  title = {{Traversing the Regioselectivity of Intermolecular Pericyclic Aryne Reactions: Total Syntheses of Laetevirenol A and Isoampelopsin D.}},
  author = {Long Huu Nguyen and Seoyeong Kim and Jiah Kim and EunHyeon Kim and Sugyeong Ha and Myeonggyo Jeong and Ki Wung Chung and Yeonjoon Kim and Seokwoo Lee and Hwayoung Yun},
  journal = {Journal of the American Chemical Society},
  year = {2026},
  month = oct,
  doi = {10.1021/jacs.6c07493},
  url = {https://europepmc.org/article/MED/42913520},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - Traversing the Regioselectivity of Intermolecular Pericyclic Aryne Reactions: Total Syntheses of Laetevirenol A and Isoampelopsin D.
AU  - Long Huu Nguyen
AU  - Seoyeong Kim
AU  - Jiah Kim
AU  - EunHyeon Kim
AU  - Sugyeong Ha
AU  - Myeonggyo Jeong
AU  - Ki Wung Chung
AU  - Yeonjoon Kim
AU  - Seokwoo Lee
AU  - Hwayoung Yun
PY  - 2026
DA  - 2026/10/01
JO  - Journal of the American Chemical Society
DO  - 10.1021/jacs.6c07493
UR  - https://europepmc.org/article/MED/42913520
AB  - Resveratrol-derived natural products feature a diverse group of stilbenoids, characterized by extensive structural variation and pharmacological potential. Herein, we document our innovation in the synthesis of laetevirenol A, a biologically captivating resveratrol dimer, and isoampelopsin D enabled by operating an aryne-based synthetic program. The synthetic strategy involves the incorporation of aryne building blocks into methylene indane/indene nuclei by harnessing their innate reactivity. A dehydro Diels-Alder cycloaddition and an aryne-ene reaction were developed to construct the carbon framework of laetevirenol A and isoampelopsin D. Attempts were made to rationalize the unexpected regioselectivity behavior of crucial benzyne reactions from both empirical and computational perspectives. Ultimately, laetevirenol A and its analogs were also biologically investigated to uncover their potential antioxidant activities. This work offers valuable insights into the regioselectivity of intermolecular pericyclic aryne reactions and serves as an example of controlling aryne regioselectivities in the synthesis of molecular targets.
SN  - 0002-7863
SN  - 1520-5126
ER  -