Scheme 1. Synthetic path for CHI1: (a) Zn, TMSCl, HCl, THF –50 °C; (b) (1) trityl fluoroborate, CH2Cl2, 0 °C; (2) NEt3, rt; (c) BBr3, CH2Cl2, 0 °C; (d) OTf2, pyridine, CH2Cl2, 0 °C; (e) 2-methoxycarbonylphenylboronic acid, Pd(PPh3)4, K3PO4, DMF, 95 °C; (f) CH3SO3H, 75 °C; (g) K2CO3, ethanolamine, 160 °C; (h) TIPSCCLi, THF, 0 °C – rt; (i) SnCl2, toluene, 120 °C.
