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Reagents and conditions: (a) NBS, (PhCO2)2, CCl4, 90 °C, 1 h; (b) NH(Bn)2, CCl4, rt, 12 h, 70%; (c) OsO4, NMO, acetone/H2O, rt, 4 h, 71%, 96:4 dr; (d) BzCl, pyridine, 0 °C to rt, 24 h, 84%; (e) H2 (1 atm), Pd(OH)2, rt, 16 h, 98% (f) 5, Et3N, n-BuOH, reflux, 16 h then KOH, EtOH 80 °C, 20 h, 42%.
