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. 2017 Jul 24;60(16):7043–7066. doi: 10.1021/acs.jmedchem.7b00484

Scheme 3.

Scheme 3

Reagents and conditions: (a) Pd(PPh3)4, PPh3, NaH, NH(BOC)2, THF/DMF, 50 °C 24 h, 42%; (b) OsO4, NMO, acetone/H2O, rt, 24 h, 89%; (c) BzCl, pyridine, 0 °C to rt, 17 h, 74%; (d) 4 N HCl in 1,4-dioxane, 0 °C to rt, 16 h, 76%; (e) 7, Et3N, nBuOH, reflux, 16 h then KOH, EtOH 80 °C, 20 h, 33%.