Reagents
and conditions: (a)
HC≡CHCH2OTHP, Pd(PPh3)2Cl2, CuI, THF, Et3N, 80 °C, 1 h, 82%; (b) t-BuOK, THF, 85 °C, 2 h, 64%; (c) NIS, DMF, DCM, RT,
1 h, 99%;(d) i. NaH, THF, RT, 30 min; ii. PhSO2Cl, 1 h,
97%; (e) bis(pinacolato)diboron, PdCl2(dppf)·DCM,
KOAc, DMF, 85 °C, 3 h, 60%; (f) i. 14, Pd(PPh3)4, THF, aq. Na2CO3, 80 °C,
18 h; ii. TFA, MeOH, H2O, 1 h, 80%; (g) 4 N HCl, 1,4-dioxane,
CH3CN, 65 °C, 1 h, 68%.