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. 2014 Jul 16;5(9):1054–1059. doi: 10.1021/ml500266x

Scheme 2. Synthesis of 33 and 35.

Scheme 2

(a) i. NaOH solution (10%), THF, 25 °C; ii. 2,2-dimethoxy-propane, PTSA, DCM, 25 °C, no purification; iii. Cs2CO3, i-PrI, DMF, 25 °C, 56% over 3 steps; (b) i. NaOH solution (10%), THF, 25 °C; ii. 2,2-dimethoxypropane, PTSA, DCM, 25 °C; iii. TMSCH2N2, MeOH, 25 °C, 72% over 3 steps; (c) i. AcOH/H2O (80:20), 50 °C; ii. Cs2CO3, i-PrI, DMF, 25 °C, 59% over 2 steps; (d) i. AcOH/H2O (80:20), 50 °C; ii. TMSCH2N2, DCM, 25 °C, 66% over 2 steps; (e) TMSOTf, NIS, DCM, −25 °C, 81% for 32 and 75% for 34; (h) H2, Pd/C, dioxane, 23% for 33 and 20% for 35.