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Synthesis of erythro-difluorinated SAHA analog (±)-4. Reagents and conditions: (a) AD-mix α, CH3SO2NH2, tBuOH, H2O, (CH3)2CO, 0 °C; (b) SOCl2, pyridine, CH2Cl2, 0 °C; (c) NaIO4, RuCl3, H2O, CH2Cl2, CH3CN, 0 °C; (d) TBAF, THF, CH3CN; (e) p-TsOH, dioxane; (f) (CF3SO2)2O, pyridine, CH2Cl2, 0 °C; (g) TBAF, THF, CH2Cl2, 0 °C; (h) LiAlH4, THF; (i) CF3CO2H; (j) DIC, HOBt, aniline, DMF; (k) ClCO2Et, Et3N, CH3OH, THF; (l) NH2OH.
