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. 2012 Apr 6;3(5):392–396. doi: 10.1021/ml3000287

Scheme 1. Preparation of Boron-Based 4-OHT Bioisosteres.

Scheme 1

Reagents and conditions: (a) Propiophenone, TiCl4, Zn, THF, reflux. (b) 2-(Dimethylamino)ethylchloride hydrochloride, Cs2CO3, DMF, 70–80 °C. (c) (CF3SO2)2O, pyridine, CH2Cl2, 0 °C–rt. (d) Inline graphic, PdCl2(dppf), KOAc, dioxane, reflux. (e) KHF2, MeOH/H2O, rt. (f) (CH3)3SiCl, CH3CN, H2O, rt.