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

Yiman Gao, Jie Liu, Cong Wei, Yan Li, Kui Zhang, Liangliang Song and Lingchao Cai ()
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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

Nature Communications, 2022, vol. 13, issue 1, 1-9

Abstract: 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.

Date: 2022
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DOI: 10.1038/s41467-022-35249-7

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