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Synthesis of the benzo[c]furan analogues of d4U 214 and 215.
Reagents and Conditions: (i) propan-1,3-diol, PTSA, toluene, 110 °C, 5 h, 75%; (ii) Ph3PCH2Br, n-BuLi, THF, 0 °C to rt, 1 h, 77%; (iii) AD-mix α, aq. t-BuOH, −10 °C to 0 °C, 1 h, 85% (ee > 99%); (iv) PivCl, TEA, toluene, −10 °C, 12 h, 78%; (v) MeOH, HCl, rt, 1 h, 72%; (vi) silylated uracil, SnCl4, C2H4Cl2, 0 °C, 2 h, 212:35%, 213:38%; (vii) aq. NaOH (1N), rt, 2 h, 93%.
