Scheme 1.
Reagents and conditions: (a) Ag2O, quinoline, 0 °C to rt, 1.5 h, 70%; (b) 2,4-pentanedione, B2O3, (n-BuO)3B, EtOAc, 85 °C, 30 min, n-BuNH2, 105 °C, 30 min, 1 N HCl, 50%; (c) B2O3, (n-BuO)3B, EtOAc, 85 °C, 30 min, piperidine, 85 °C, 30 min, 0.5 N HCl, 50 °C, 30 min, 55%; (d) MeOH, 1 N NaOH, 50 °C, 1 h, 50% formic acid, 70 %.