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. 2019 Aug 1;1(1):fcz008. doi: 10.1093/braincomms/fcz008

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© The Author(s) (2019). Published by Oxford University Press on behalf of the Guarantors of Brain.

This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted reuse, distribution, and reproduction in any medium, provided the original work is properly cited.

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Synthesis of clemalogues. Summary of synthetic routes used to prepare clemalogues 1–28. (a) cyclopentylacetic acid, PPA, μw, 80°C, 20%; (b) ClCH₂(4-ClPh), K₂CO₃, DMF, 60°C, 67%; (c) ethyl 4-Cl-3-oxobutanoate, SnCl₂, EtOH, 80°C; (d) pyrrolidine, EtOH, 95°C; 83% for two steps (e) Br-CH₂R, NaH, THF, 0°C to rt, 15–60% or Br-CH₂R, NaH, TBAI, THF, 0°C to rt, 13–54% or propyl iodide, NaH, THF, 0°C to rt, 47%;(f) p-Cl-benzylchloride, NaH, DMF, rt, 54%; (g) (i) LiOH, MeOH/water, rt, (ii) pyrrolidine, HATU, DIEA, DMF, rt, 43% over 2 steps; (h) p-Cl-benzylchloride, K₂CO₃, CH₃CN, 45°C, 85% or cyclohexylmethyl bromide, K₂CO₃, TBAI, CH3CN, 55°C, 30%; (i) pyrrolidine, Na(OAc)₃BH, CH₂Cl₂; 30–46%; (j) ClCH₂Ar, K₂CO₃, CH₃CN, 45°C, 44%; (k) pyrrolidine, Na(OAc)₃BH, CH₂Cl₂, rt, 65%; (l) HNR₂, Na(OAc)₃BH, CH₂Cl₂, rt, 47–85%; (m) H₂, Pd/C, MeOH, rt, 55%; (n) 4 M HCl in dioxane, rt.