With key pyrrolidine 8 in hand, two distinct approaches to the natural product were explored, differentiated by the means with which the C-4'oxidation would be installed: (1) C-H oxidation and ( ) decarboxylative chlorination. To set the stage for the C-H oxidation, glycosylation donor 9 (AgOTf, NIS, 79% yield) followed by desilylation (TBAF/AcOH, 83%) delivered cyclization precursor 10. The electron-rich benzylic system present in 10 is innately primed to achieve a benzylic C-H functionalization to provide the 9-membered ring through either direct or indirect means. For instance, the use of DDQ (DCE, 100 °C, µW) led to 3-10% yield of the desired product 11 but unfortunately was not reproducible or scalable despite extensive efforts. Switching to an I(III)-based oxidant (PIFA, benzene, hn) 10 delivered a mixture of diastereomeric benzylic trifluoroacetates that were purified before exposure to (+)-CSA (1.0 equiv, ACN, 60 °C) to afford 11 in 45% yield (over two steps) as a 5:1 mixture of diastereomers. This two-step process was serviceable for exploring the downstream C-4' oxidation chemistry. The structure of 11 was confirmed by X-ray crystallographic analysis after debenzoylation (12).