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. Author manuscript; available in PMC: 2016 Aug 15.
Published in final edited form as: Bioorg Med Chem Lett. 2015 May 11;25(16):3382–3389. doi: 10.1016/j.bmcl.2015.04.103

Scheme 2.

Scheme 2

Synthesis of TX1-85-1. Reagents and Conditions: (i) 1, 4-dioxaspiro[4.5]decan-8-ol, Ph3P, DEAD, THF, rt; (ii) acetone, 5 M HCl, 45% for 2 steps; (iii) 1-acetylpiperazine, Na(OAc)3BH, ClCH2CH2Cl, rt, 62%; (iv) 3-nitro-4-fluorophenylboronic acid, PdCl2(PPh3)2, K2CO3, dioxane/H2O (3:1), 100 °C, 75%; (v) phenol, K2CO3, DMF, 80 °C, 90%; (vi) Raney Ni, H2, MeOH, rt; (vii) acryloyl chloride, THF, NaHCO3, 0 °C, 35% over 2 steps.