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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 28.

Scheme 28

Reaction conditions: (a) (BnO)2P(O)CH2CO2H, DCC, CH2Cl2, 73%; (b) TFA, H2O, 5 min, up to 62%; (c) reagent 173, 5-Ph-1H-tetrazole, CH2Cl2, then 3-chloroperoxybenzoic acid, CH2Cl2, up to 93%; (d) H2, Palladium hydroxide/carbon, MeOH, H2O, 50 psi, 92%; (e) BnBr, NaH, DMF, 55%; (f) (BnO)2P(O)CH2CO2H, EDAC, DMAP, CH2Cl2, 95%; (g) H2, Palladium hydroxide/carbon, MeOH, TEAB(aq) 79%; (h) H2, Palladium hydroxide/carbon, MeOH, H2O, 50 psi, 79%.