Photoinduced β-fragmentation of aliphatic alcohol derivatives for forging C–C bonds
Yiman Gao, Jie Liu, Cong Wei, Yan Li, Kui Zhang, Liangliang Song, Lingchao Cai
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.