One-pot transformation of simple furans into 4-hydroxy-2-cyclopentenones in water.

A highly efficient one-pot transformation of readily accessible furans into 4-hydroxy-2-cyclopentenones in H2O, using singlet oxygen as oxidant, has been developed.

Green oxidations of furans--initiated by molecular oxygen--that give key natural product motifs.

In this article, we explore how changes in the positioning of pendant hydroxyl functionalities in the photooxygenation substrate dramatically alter the course of furan oxidations that are initiated by singlet oxygen; and, how these different reactivities can be harnessed through cascade reaction sequences to access, rapidly and effectively, a broad range of important natural product motifs.

Singlet oxygen initiated cascade transformation of a simple difuran into the key ABC-ring motif of the pectenotoxins.

The key ABC-ring motif of the pectenotoxins has been synthesized, starting from a simple and readily accessible difuran precursor, using a complex singlet oxygen-mediated cascade reaction sequence.