Despite the wealth of literature on the ring-opening of OBDs, there are few reported methods capable of accessing the substitution required for NOG. Most reported OBD ringopenings introduce substitution on the cyclohexane ring located β to the newly generated alcohol; anthracyclines typically do not have substitution at this position. Thus, we opted to first synthesize a model OBD 18 (Scheme 3) to evaluate the likelihood of success in the application of known literature conditions to the advanced OBD scaffold that is needed for NOG.