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

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.