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Reagents and conditions (a) (PhSeO)2O, CH2Cl2, 23 °C, 15 min (82%); (b) TBAF, THF, 23 °C (91%); (c) 54, EDCI, DMAP, CH2Cl2, 23 °C (91%); (d) Tf2O, DMSO, DMSO, –40 °C; DIPEA, 0 °C; t-BuOH, 0 °C; 56, 23 °C; Ac2O, 23 °C; (e) n-Bu3SnH, PdCl2(PPh3)2, AcOH, CH2Cl2, 23 °C (84%); (f) [N-methylpyridinium-4-carboxaldehyde]+I, DBU, DMF, CH2Cl2, 23 °C (70%); (g) 59, silica gel, EtOH (58%); (h) CF3CO2H, THF/H2O; (i) AgNO3, H2O, (77%, 2 step).
