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. 2017 Feb 3;12(2):e0170301. doi: 10.1371/journal.pone.0170301

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© 2017 Zhou et al

This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

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Fig 2 — Reagents and conditions: (i) triethyl phosphonoacetate/t-BuOK, THF; (ii) Me₃S(O)I, t-BuOK, DMSO; (iii) K₂CO₃, MeOH, reflux; (iv) diphenylphosphoryl azide, Et₃N, t-BuOH, toluene, reflux; (v) NaH, 1-chloroacetyl-4-methylpiperazine, DMF; (vi) HCl/MeOH; (vii) aldehyde, NaBH₃(CN), AcOH; (viii) Ac₂O for compound 22 or PhNCO for 23; (ix) Aryl-CHO; (x) CHBr₃, KOH; (xi) MeMgBr, Ti(O-i-Pr)₄; (xii) Mg, then Boc-N = N-Boc; (xiii) NaH, then 1-chloroacetyl-4-(Boc)piperazine for 32 or 1-chloroformyl-4-(Boc)piperazine for 33; (xiv) (Boc)₂O, Et₃N; (xv) PhBr, CuI, Pd(dppf)Cl₂, (i-Pr)₂NEt.