An Exploratory Synthesis of a Chemical Group Common to Several Novel Biflavonoid Molecules

In 2014, a biochemical assay of the Kenyan plant Ochna Holtzii Gilg led to the discovery of eight new molecules containing a flavonoid group. In this investigation, we are synthesizing a group containing a bicyclic ring, which was common to the compounds isolated in the 2014 assay. We intend to study the anti-microbial activity of the group compared to structurally similar molecules, to study the usefulness of this chemical in a targeted in vivo role. In this investigation, we attempted two synthesis routes for flavonoid-like compounds. In the first route, we attempted a synthesis based on acid cyclization, and in the second, we used various aldehydes and an acetophenone to synthesize the three-ring flavonoid base group, using several reactions to demonstrate the versatility of our process. In the first synthesis route, chromatography techniques were used extensively in the purification of intermediate products. Additional analogs were synthesized via a second synthetic sequence. Findings regarding the second synthesis route will be presented at IMSAloquium