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Reagents and conditions: (i) NCS, pentane; (ii) LiTMP, −78 °C, 36% over two steps; (iii) nBuLi, MeCN, THF, −78 °C then tetramethylpiperidine −78 °C, 100%; (iv) (Boc)2O, CH2Cl2; (v) tBuOCH(NMe2)2, DMF, 70 °C; (vi) THF, AcOH, H2O, 72% from 7; (vii) H2NCH2CO2Et·HCl, NaOAc, MeOH (viii) ClCO2Bn, DBU, CH2Cl2, reflux, 67% from 10; (ix) H2, Pd/C, EtOH; (x) H2NCH=NH·AcOH, EtOH, reflux, 91% from 12 and (xi) TFA, 81%.
