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. Author manuscript; available in PMC: 2017 Dec 7.
Published in final edited form as: J Am Chem Soc. 2016 Nov 28;138(48):15563–15570. doi: 10.1021/jacs.6b10354

Scheme 2. Synthesis of the Unsaturated Imine 15a and the Pyridone 17a and Structures of the N-Methyl Amide Derivatives 15b and 17ba.

Scheme 2

aStructures of the N-methylamides 15b and 17b. Reagents and conditions: (a) silver trifluoroacetate (AgOTFA), Et3N, DMF, 0 °C; (b) concentrate from 0.5% HCO2H–5% CH3OH–CH3CN, 23 °C, 87% (two steps); (c) propylphosphonic anhydride solution (T3P), N-methylmorpholine, N,Ndimethylethylenediamine, THF, 23 °C, 93%; (d) trifluoroacetic acid (TFA), CH2Cl2, 0 °C; aqueous NaHCO3, 23 °C, 62%; (e) K2CO3, CH3OH, 0 → 23 °C, 78% (two steps); (f) T3P, N-methylmorpholine, N,N-dimethylethylenediamine, THF, 23 °C, 46%; (g) TFA, CH2Cl2, 0 °C, 86%.