In search of a more systematic way to interrogate structureactivity relationships surrounding 1, we considered a divergent approach to the ophiobolins that would facilitate late-stage diversification of the A-and C-rings. Following this logic, we envisioned that the A-ring stereotriad ( ) could be established via a stereospecific [1,2]-rearrangement of epoxide 7 (Scheme 1), 17 which itself could be prepared from directed oxidation of Scheme 1. A Strategy to Access the 5-8-5 Carbotricycle of 1.