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Reagents and conditions: (i) For 2a, MeNO2, HOAc, for 2b EtNO2; NH4OAc, reflux (ii) for 3a Dioxane/DMF, for 3b EtOH; NaBH4, 0 °C (iii) Raney Ni, NH2NH2·H2O, MeOH, 50 °C (iv) Ac2O, TEA, DCM, 0 °C to rt (v) (CH2O)n, p-TsOH, PhMe, 120 °C (vi) KOH, EtOH/water, reflux (vii) ArCH2Cl,* TEA, EtOH, 130 °C, microwave (viii) H2, Pd/C, EtOH/THF (ix) H2NSO2Cl, DMA, 0 °C to rt: *R2a = H, b = 2′-MeO, c = 3′-MeO, d = 4′-MeO.
