Synthesis and Utilization of Novel Chromone Based Scaffolds

Abstract

The chromone moiety (11) is a common structural motif found in a wealth of natural products and medicinally relevant compounds. Its synthesis has been investigated for over 100 years, yet opportunities still remain for the development of synthetic methods which provide a broader substrate scope and increased efficiency.

The synthesis of 3 from 4 was discovered by members of our group, which provided a novel way of accessing the chromone scaffold. This new method showed promising signs of overcoming problems encountered in established synthetic methodology and provided chromones in moderate to good yields (30 – 60%). Additionally, this method provides functional handles, not accessible by established methodology, which we envisioned could be used to provide access to further elaborated natural product-like scaffolds.

This project investigated the scope of this reaction by varying portions of the molecule. The synthetic utility of the reaction was then explored by attempting a number of modifications to the relevant chromones, most notably the divinyl cyclopropane rearrangements to access chromone fused cycloheptadienes (76).