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Photoinduced β-fragmentation of aliphatic alcohol derivatives for forging C–C bonds

Author

Listed:
  • Yiman Gao

    (Nanjing Forestry University)

  • Jie Liu

    (Nanjing Forestry University)

  • Cong Wei

    (Nanjing Forestry University)

  • Yan Li

    (Nanjing Forestry University)

  • Kui Zhang

    (Nanjing Forestry University)

  • Liangliang Song

    (Nanjing Forestry University)

  • Lingchao Cai

    (Nanjing Forestry University)

Abstract

Alcohols are ubiquitous in chemistry and are native functionalities in many natural products and bioactive molecules. As such, a strategy that utilizes hydroxy-containing compounds to develop bond disconnection and bond formation process would achieve molecular diversity. Herein we utilize bench-stable N-alkoxyphthalimides prepared from alcohols to couple with glycine derivatives via radical process under visible light irradiation, providing a variety of unnatural amino acid (UAA) and peptide derivatives. The approach allows to rapidly deconstruct molecular complexity via β-fragmentation such as saclareolide, β-pinene and camphor and provides products with unique scaffolds, which show inhibition toward the pathogenic fungi growth.

Suggested Citation

  • Yiman Gao & Jie Liu & Cong Wei & Yan Li & Kui Zhang & Liangliang Song & Lingchao Cai, 2022. "Photoinduced β-fragmentation of aliphatic alcohol derivatives for forging C–C bonds," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
  • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-35249-7
    DOI: 10.1038/s41467-022-35249-7
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    References listed on IDEAS

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    1. Jason W. Chin, 2017. "Expanding and reprogramming the genetic code," Nature, Nature, vol. 550(7674), pages 53-60, October.
    2. Qing Zhang & Fu-Min Zhang & Chang-Sheng Zhang & Si-Zhan Liu & Jin-Miao Tian & Shao-Hua Wang & Xiao-Ming Zhang & Yong-Qiang Tu, 2019. "Enantioselective synthesis of cis-hydrobenzofurans bearing all-carbon quaternary stereocenters and application to total synthesis of (‒)-morphine," Nature Communications, Nature, vol. 10(1), pages 1-7, December.
    3. Yuchao Zhu & Kaimeng Huang & Jun Pan & Xu Qiu & Xiao Luo & Qixue Qin & Jialiang Wei & Xiaojin Wen & Lizhi Zhang & Ning Jiao, 2018. "Silver-catalyzed remote Csp3-H functionalization of aliphatic alcohols," Nature Communications, Nature, vol. 9(1), pages 1-7, December.
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