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. Author manuscript; available in PMC: 2011 Dec 23.
Published in final edited form as: J Med Chem. 2010 Nov 23;53(24):8716–8726. doi: 10.1021/jm101048k

Scheme 3.

Scheme 3

Synthesis of Hydroxy- and Aminopropyl Derivatives 28–30a

aReagents and conditions: (a) RNH2, MgSO4, CHCl3, room temperature, overnight; (b) 9, CHCl3, room temperature, 18 h; (c) TMSCHN2, CH3OH/THF (1:3), −10 to 0 °C, 30–45 min; (d) DDQ (2.2 equiv), 1,4-dioxane, reflux, 3–4 h; (e) KOH, water/ethylene glycol (1:3), reflux for 24 h for 28, or morpholine, DMF, reflux 18 h for 29, or imidazole, DMF, reflux 18–20 h for 30.