Polyheterocycle-carbohydrate chimeras: photoassisted synthesis of 2,5-epoxybenzoxacines and 2,5-epoxybenzazocine scaffolds and their postphotochemical hydroxylations

Abstract

AbstractPhotoassisted synthesis of complex polyheterocyclic molecular architectures via excited state intramolecular proton transfer (ESIPT) is for the first time implemented for the reactions of o-keto phenols. This adds the 2,5-epoxybenzoxacine core to the previously obtained 2,5-epoxybenzazocine cores and offers rapid access to primary photoproducts which lend themselves to diverse yet simple postphotochemical modifications to further grow the complexity of the target structures, specifically – access to polyheterocycle-carbohydrate chimeras containing up to five contiguous stereogenic centers and benzazocine or benzoxacine heterocyclic cores.