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. Author manuscript; available in PMC: 2013 Sep 1.
Published in final edited form as: Bioorg Med Chem. 2012 Jul 14;20(17):5181–5187. doi: 10.1016/j.bmc.2012.07.006

Scheme 10.

Scheme 10

One enantiomer series present in the racemic mixtures is drawn to illustrate relative stereochemistry. (a) (i) MsCl, i-Pr2NEt, CH2Cl2, rt 15 min, (ii) NaSMe, DMF, rt, 1 h, 86%; (b) LAH, THF, rt, 18 h, 57%; (c) 9-deazaadenine, CH2O, 1,4-dioxane, H2O, 85 °C, 15 min, 68%; (d) aq. HCl (37%), MeOH, rt, 79%.