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Reagents and conditions: (a) Pyridine-sulfur trioxide complex, NEt3, DCM, DMSO, 60%; (b) Bestmann-Ohira reagent, K2CO3, MeOH, 72%; (c) 4-fluorobenzaldehyde oxime, PIFA, MeOH, H2O, 52%; (d) 4M HCl in 1,4-dioxane, 100%; (e) 2-ethoxybenzene sulfonyl chloride, DIEA, DCM, 55%; (f) 1-azido-4-fluorobenzene, sodium ascorbate, CuSO4, tert-BuOH, H2O, 56%; (g) 4M HCl in 1,4-dioxane, 100%; (h) 2-ethoxybenzene sulfonyl chloride, NEt3, DCM, 31%.
