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. Author manuscript; available in PMC: 2016 Dec 14.
Published in final edited form as: Angew Chem Int Ed Engl. 2015 Dec 22;55(5):1614–1650. doi: 10.1002/anie.201502227

Scheme 6.

Scheme 6

Reaction conditions: (a) NaBH4, MeOH, 0°C, 30 min., 97%; (b) Pd(OH)2 on carbon, H2, MeOH, 12 h, quantitative yield; (c) H2SO4 (conc.), Me2C=O, 0°C, 1 h 83%; (d) Tf2O, pyridine, CH2Cl2, rt, 1 h, 89%; (e) CF3CO2Cs, 18-crown-6, toluene, DMF, 80°C, 1.5 h, then saturated NaHCO3, rt, 1 h, 78% from 57; (f) TFA, MeOH, 60°C, 3 h.