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. 2012 Sep 9;3(11):920–924. doi: 10.1021/ml300197h

Scheme 2. Synthesis of Diastereomers of Lead Compound.

Scheme 2

Enantioselective synthesis of diastereomers. (a) MeI, NaHCO3, DMF. (b) DIBAL, MeOH. (c) NaHSO3, KCN. (d) TBSCl, imidazole, DMF. (e) H2, 5% Rh/C, EtOH/NH3. (f) Benzaldehyde, NaCNBH3, MeOH. (g) AcCl, Et3N, CH2Cl2. (h) HCl, dioxane. (i) Cbz-Cl, Et3N, CH2Cl2. (j) HF/pyridine, acetonitrile.