Scheme 3. Synthetic Routes toward Subsite 3 Iodophenol Analogues Bearing Alkyl Chains.

Conditions: (a) acetone, TFAA, TFA, 0 to 25 °C, 24 h, 45%; (b) NIS, THF, 0 °C, 1 h, 73%; (c) R₁OH, DIAD, PPh₃, THF, 0 °C, 2.5 h, 63–68%; (d) EtI, Cs₂CO₃, DMF, 25 °C, 20 h, 57%; (e) 1 N aq. NaOH, THF, 25 °C, 1 h, 77–88%; (f) R-I Cs₂CO₃, DMF, 80 °C, 2–4 h, 57–72%; (g) BCl₃, CH₂Cl₂, 0 to 25 °C, 30 min; (h) 1 N NaOH (aq.), MeOH, THF, 25 °C, 2–5 days, 33–64% over 2 steps, (i) I(CH₂)₄I, Cs₂CO₃, DMF, 80 °C, 2.5 h, 34%; (j) NIS, AcOH, 25 °C, 1 h, 88–98%.