Synthesis of imidazole fused natural products and bioactive compounds | Poster Board #3618

Imidazole is a five-membered heterocyclic compound with two nitrogen and three carbon in its structure. Imidazoles are important in medicinal chemistry because of the electron-rich nitrogen atoms in their structure which are responsible to bind with various proteins, enzymes, or receptors readily. Imidazole is well known because of its different biological activities such as antibacterial, antitumor, antifungal, etc. We have developed a novel approach to synthesize imidazole fused with nootkatone. Nootkatone has been isolated from grapefruit and is used as an approved insecticide. In the synthetic process, firstly, the α,β-unsaturated functional group of nootkatone was transformed into epoxyketone by reacting with sodium hydroxide and hydrogen peroxide. Secondly, the epoxyketone was reacted with imidines to form imidazole fused products. Lithium bis(trimethylsilyl)amide was used as a base in the reaction. The reaction was carried out at 0 °C in a nitrogen atmosphere. A series of novel imidazole fused molecules were synthesized with good yield. Some of the compounds were purified by recrystallization. We are developing fused imidazoles with other natural products such as ethisterone, progesterone, and bisnoralcohol.