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. Author manuscript; available in PMC: 2020 Oct 16.
Published in final edited form as: Bioorg Med Chem. 2010 May 25;18(14):5208–5223. doi: 10.1016/j.bmc.2010.05.057

Scheme 4.

Scheme 4.

Synthesis of aryl aldehydes 54, 56, 58, 59, 62, and 64. Reagents and conditions: (a) i-BuOCOCl, Et3N, THF then NaBH4, H2O; (b) MnO2, DME; (c) BBr3, CH2Cl2; (d) 4-fluorobenzaldehyde, K2CO3, DMA, 150 °C; (e) NaOH, MeOH; (f) EDC, HOBt, MeNH2, DMF; (g) H2, 5% Pd/C, AcOEt; (h) MsCl, pyridine, THF; (i) DIBAL, THF.