A chemoselective epoxidation with MCPBA on enyne 16 afforded lactone 17 (through an intramolecular cyclization of the α-epoxide) and β-epoxide 18 in 35% and 51% yields respectively. The lactone 17 was then converted to alcohol 19 in 78% yield via a one-pot process using Ac2O followed by the addition of TBAF. In parallel, epoxide 18 was treated with KOH in DMSO at 145 °C which incidentally lactonized onto the methyl ester, and deprotected the primary alcohol to afford 19 in a 44% yield. A one-pot oxidation with DMP followed by the addition of trimethyl orthoformate and amberlyst 15® gave the dimethyl acetal 20 in 75% yield. Reduction of the lactone unit with DIBALH led to lactol 21 in 90% yield (dr = 5:1) which, after treatment with anhydrous HCl and then with Ac2O, produced anomers 22 and 23 in 96% combined yield (dr = 1.6:1). Both anomers 22 and 23 were separated at this point by silica gel chromatography to facilitate further functionalization, purification, and characterization.