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. Author manuscript; available in PMC: 2020 Feb 26.
Published in final edited form as: Eur J Med Chem. 2018 Dec 28;164:471–498. doi: 10.1016/j.ejmech.2018.12.054

Scheme 9a.

Scheme 9a

aReagents and conditions: (a) Styrene, P(o-tolyl)3, NEt3, Pd(OAc)2, DMF, 100 °C, 18 h; (b) (i) NaOH (aq), THF/H20, reflux or dioxane/H20, rt, (ii) 2 M HCI (aq); (c) H2, 10% Pd/C, THF or dioxane, rt, 18 h; (d) NHMe2, 0 °C, 2 h; (e) Tf20, NEt3, DCM, −10 °C, 2 h; (0 CO, DPPP, NEt3, Pd(OAc)2, MeOH/DMF, 80 °C, 24 h; (g) (i) LiOH, dioxane/H20, rt, 18 h, (ii) 1 M HCI (aq).