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. 2018 Oct 19;3(10):13647–13666. doi: 10.1021/acsomega.8b01481

Scheme 1. Synthesis of N-Terminus Fragments 3a–k.

Scheme 1

Reagents and conditions: (a) aq. NaOH, MeOH, rt; (b) aq. HCl, 49–73%; (c) BnOH, DMAP, DCC, DMF, rt, 91%; (d) MeI or BnBr, NaH, DMF, 0 °C, 86–88%; (e) H2, Pd–C, MeOH, rt or aq. LiOH, THF-DME, rt, 80–98%; (f) SOCl2, MeOH, 0 °C to rt, quant; (g) NaBH4, EtOH, 0 °C, 77%; and (h) Tf2O, pyridine, CH2Cl2, −35 °C, 45%.