Reagents and conditions: (a)
ethylene glycol, toluene, TsOH, 100 °C, 98%; (b) DPPA, DEAD,
PPh3, THF, 87%; (c) trimethylphosphine, THF/H2O, 85%; (d) formaldehyde, EtOAc, MeOH, 92%; (e) TsOH, acetone, 98%;
(f) KHMDS, PhN(SO2CF3)2, THF, 95%;
(g) Pd(PPh3)2Cl2, 7-isoquinoline boronic acid,
Na2CO3, dioxane/H2O, 76%; (h) KOOCN=NCOOK,
AcOH, DMSO, THF, 70%.