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. Author manuscript; available in PMC: 2014 Aug 11.
Published in final edited form as: Bioorg Med Chem. 2013 Nov 12;22(1):435–439. doi: 10.1016/j.bmc.2013.11.006

Scheme 1.

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 %.