hallmark 9-membered ring using a bold dipolar cycloaddition approach (Gen 1) failed due to instability of the acyclic precursor. Next, intramolecular glycosylation (the successful strategy employed by Nakata) was explored, but unfortunately the completely functionalized precursor did not form the desired ring (Gen 2). Reasoning that an abundance of functional groups prevented cyclization, an oxidative furan-based approach was evaluated which also failed due to the formation (in low yield) of the undesired endo-cyclization product (Gen 3).