Scheme 3. Synthesis of RXR Ligands 9, 12, 13, 19 and 28.
Reagents and conditions: (a) Pd(PPh3)4, dioxane, H2O, rt, 5.5 h, 26%; (b) LiOH, EtOH, H2O, THF, rt, 15–18 h, 74–84%; (c) Pd(PPh3)4, dioxane, H2O, rt, 3.5 h, 24%; (d) Pd(PPh3)4, dioxane, H2O, rt, 24 h, 71%; (e) Pd(PPh3)4, dioxane, H2O, rt, 16 h, 4–16%.