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. 2014 Feb 13;5(5):550–555. doi: 10.1021/ml400528y

Scheme 3. Synthesis of the C-Methylated α,α-Disubstituted Analogues 32–35 with a 3-Carbon Spacer.

Scheme 3

Reagents and conditions: (1) SOCl2, MeOH, 0 °C to r.t., 12 h, 99%; (2) HBr(g), cat. mCPBA, PhMe, 0 °C, 2 h; (3) 10c, Cs2CO3, DMF, r.t., 4 h; (4) aq. LiOH, THF, reflux, 12 h, 52% (3-steps); (5) HBTU, Hünig’s base, THF, r.t., 65 to 85%; (6) TFA, CH2Cl2 (1:1, v/v), 0 °C to r.t., 65 to 75%.