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Reagents and conditions: (a) pyruvic aldehyde, EtOH, 25 °C; (b) p-dimethylaminobenzaldehyde, piperidine, AcOH, toluene, reflux; (c) Bu4Sn, Pd(Ph3)4, toluene, reflux; (d) I2, CHCl3, 25 °C; (e) (1) Cu(acac)2, LiOH·H2O, N1,N2-bis(4-hydroxy-2,6-dimethylphenyl)oxalamide, dimethyl sulfoxide (DMSO)/H2O, 80 °C, (2) 2-fluoroethyl p-toluenesulfonate, Cs2CO3, DMF, 95 °C.
