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. 2014 Apr 21;57(10):4111–4133. doi: 10.1021/jm500010b

Scheme 1. Synthetic Route for 1 and Analogues.

Scheme 1

Reagents and conditions: (a) NIS, TFA, reflux, 24 h; (b) HS(CH2)nCOOCH3 (n = 1, 2), Pd(OAc)2, Xantphos, Cs2CO3, LiI, ZnCl2, THF, 60 °C, overnight, or HS(CH2)3CH3, Pd2(dba)3, Dppf, Et3N, NMP, 80 °C, 2 h, or HCC(CH2)nOH (n = 1, 2), Pd(PPh3)2Cl2, CuI, Et3N/THF, 60 °C, 2 h (4:1), 60 °C, 2 h; (c) Fe, AcOH, 70 °C, 1 h, or Pd/C, H2 30 psi, EtOH/EtOAc (6:1), rt, overnight; (d) RSO2Cl, pyridine, CH2Cl2, rt, overnight, or RCOCl, Et3N, CH2Cl2, rt, overnight, or Inline graphic, CH3CN, 80 °C, 15 h; (e) BBr3, CH2Cl2, 0 °C to rt, 1 h, or BBr3, CH2Cl2, 0 °C to rt, 1 h, quench with MeOH at 0 °C; (g) phenyl boronic acid, Pd(PPh3)4, Na2CO3, THF/H2O, 60 °C, 2 h; (h) NH4OH, rt, 1 h; (i) NaN3, SiCl4, CH3CN, 80 °C, 15 h; (j) LiOH, THF, rt, 1 h; (k) H3CCOCl, Et3N, 0 °C, rt, 30 min.