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Reagents and conditions: (a) K2CO3, DMF, 0 or 100 °C. (b) NaBH4, CH3OH. (c) MOMCl, DIPEA. (d) n-BuLi, B(i-PrO)3, −78 °C to room temperature. (e) HCl. (f) NaIO4, MeOH−H2O, 60 °C, 1 h or 1 equiv of m-CPBA, DCM−THF, −20 °C. (g) NaIO4, 60 °C, 12 h or 2 equiv of m-CPBA, −60 °C to room temperature. (h) Bis(pinacol-diboron), PdCl2(dppf)2, KOAc, dioxane. (i) NaBH4, EtOH.
