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Reagents and conditions: (a) BnBr, K2CO3, acetone, reflux, 7 h; (b) NaOH, THF, H2O, 70 °C, 150 min; (c) EtNH2·HCl, DIPEA, DMAP, EDC·HCl, DCM, 15 h; (d) Pd/C (10 wt % loading), formic acid, tBuOH, 50 °C, 2 h; (e) NaOH, H2O, reflux, 2 h; (f) 3,4-dihydro-2H-pyran, TsOH·H2O, EtOAc, DMF, overnight; (g) (i) 4-nitrobenzyl alcohol, DIPEA, DMAP, EDC·HCl, DCM, overnight (ii) TFA, 5 min; (h) (i) RCH2Br, DIPEA, DMF, 90 min to 2 h (ii) TFA, 10–12 min.
