Brian C. Goess, Justin Goodwin, and Ashley Windrum. Furman University, Greenville, SC
The goal of our research is to synthesize hibiscone C and a number of cyclopropyl analogs. Hibiscone C is a natural product which has a structure related to that of another naturally occurring compound wortmannin. Wortmannin has been shown to bind to the PI-3 kinase and affect cell growth in colorectal tumors as well as breast cancer cells. Unfortunately this PI-3 kinase also regulates cell growth in several normal body cells, and wortmannin has not yet been shown to demonstrate selectivity between these cells and cancerous cells. Wortmannin also exhibits a high reactivity and will react with water. Due to this lack of selectivity and high reactivity, wortmannin cannot currently be practically implemented as a cancer treatment. Because cyclopropanes and alkenes exhibit similar reactivity but cyclopropanes are less reactive, we are undertaking a synthesis of a potentially more efficacious cyclopropyl homolog of hibiscone C. We currently have recreated the first six steps of a known synthesis of hibiscone C and will describe our progress towards a cyclopropyl homolog.