Progress toward a Novel, Umpolung Style Approach to the Synthesis of Cyclic 1,2-Diketones

Abstract

The preparation of cyclic 1,2-diketones, especially those of medium ring size, is an important topic in organic synthesis. This class of compound is a useful synthetic building block and the 1,2-dicarbonyl moiety is featured in a range of biologically active compounds. Here, a novel approach to the synthesis of small, medium, and large cyclic 1,2-diketones is presented. The method showcases an Umpolung style one atom ring contraction to convert a cyanohydrin lactone to the corresponding 1,2-diketone. Although the syntheses were ultimately unsuccessful due to difficulties with ring closure, the Umpolung reaction elicited the desired 1,2-diketone in an aliphatic system. It is my hope that this work will serve as a basis for further investigation into the use of this Umpolung reaction for cyclic 1,2-diketone synthesis. Recommendations for future work, in particular suggestions for further attempts at ring closure, are proposed.