Hexahydroxanthenes are not abundant in nature, but they are a key feature in the schweinfurthins and some related natural products. The anticancer activity of the schweinfurthins, together with the difficulties encountered in efforts at repeated isolation, has drawn attention to their synthesis. As part of our ongoing efforts to elucidate structure activity relationships in the 3-deoxyschweinfurthin (3) series we required larger amounts of the hexahydroxanthene 2 which is available via a cascade cyclization of the epoxide 1. In this presentation, we will discuss a novel route to the R,R,R enantiomer of the hexahydroxanthene 2 that employs asymmetric epoxidation methodology to install the initial stereocenter in the epoxide 1.