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. 2015 Apr 13;54(21):6217–6221. doi: 10.1002/anie.201501394

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© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

© 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

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Scheme 2 — Synthesis of analogues for SAR studies around the lead scaffold. Reagents and conditions: a) R³CHO, NH₄OAc, EtOH, 90 °C, 26–86 %, d.r. 2:1–>20:1; b) NiCl₂⋅6 H₂O, NaBH₄, MeOH, 0 °C; c) Boc₂O, 39–91 % (2 steps); d) 4, [Pd₂(dba)₃], Xantphos, Cs₂CO₃, 1,4-dioxane, 100 °C, 2–75 %; e) 4, K₃PO₄, CuI, (±)-trans-1,2-diaminocyclohexane, 1,4-dioxane, 97 °C, 7–65 %; f) HCl/dioxane, 96 %; g) R²Cl, TEA, CH₂Cl₂ or RNCO, CH₂Cl₂, 12–60 %. Boc=tert-butyloxycarbonyl, TFA=trifluoroacetic acid.