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a (1) Oxalyl chloride, dry DCM, DMF, rt, 2 h, (2) 4, pyridine, CH3CN, overnight, CH3OH; b NaBH4, CH3OH, 0 °C, 1 h; c I2, KOAc, EtOH, 2 h; d (1) oxalyl chloride, dry DCM, DMF, rt, 2 h, (2) 4, pyridine, CH3CN, overnight; e Pd/C, H2, CH3OH, rt, 3 h; f (1) 1, 7-Dibromoheptane, potassium tert-butoxide, dry DMF, rt, 2 h, (2) HCl (12 N), DCM, 2 h; g 1, CH3CN, overnight, reflux; h sodium hydroxide, CH3OH : H2O = 2:1, reflux, overnight.
