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Synthesis of 16, a (1S,2R,3S,4R)-4-aminocyclopentane-1,2,3-triol derivative of PreQ0. Reagents and conditions: (a) Pd(PPh3)4, PPh3, NaH, NH(Boc)2, THF/DMF, 1 day, 50 °C, 42%; (b) OsO4, NMO, acetone/H2O, 1 day, rt, 83%; (c) BzCl, pyr, 17 h, 0 °C to rt, 74%; (d) 4 M HCl in 1,4-dioxane, 16 h, 0 °C to rt, 76%; (e) 9, Et3N, n-BuOH, 16 h, 130 °C; (f) KOH, n-BuOH/EtOH, 16 h, 80 °C, 33%.
