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. Author manuscript; available in PMC: 2009 Dec 25.
Published in final edited form as: J Med Chem. 2008 Dec 25;51(24):8158–8162. doi: 10.1021/jm801254r

Scheme II.

Scheme II

Synthesis of designed Smac mimetics.

Reagents and conditions: (a) 4 N HCl in 1,4-dioxane, methanol, rt, overnight, 95%; (b) i. formaldehyde (37% in water), NaBH3CN, HOAc, methanol, rt, overnight; ii. 4 N HCl in 1,4-dioxane, methanol, rt, overnight, 71% over two steps; (c) i. BnBr, NaHCO3, 1,4-dioxane, rt, overnight; ii. 4 N HCl in 1,4-dioxane, methanol, rt, overnight, 77% over two steps; (d) i. Ac2O or BnCOCl, N,N-diisopropylethylamine, CH2Cl2, rt, overnight; ii. 4 N HCl in 1,4-dioxane, methanol, rt, overnight; 85% for 5 and 87% for 6 over two steps.