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Modified synthetic route to viniferifuran. Reagents and conditions: a) ArBr or ArI (1.5–2 equiv.), Pd(OAc)2 (0.1 equiv.), PCy3⋅HBF4 (0.2 equiv.), K2CO3 (1.5 equiv.), PivOH (3 equiv.), 100 °C, 20 h, 35–74%. b) ArBr (1.5–2 equiv.), PdCl(C3H5)(dppb) (0.05 equiv.), KOAc (2 equiv.), DMA, 150 °C, 20 h, 47–60%. c) Phosphonate derivatives (1.5 equiv.), NaH (3 equiv.), THF, 120 °C, MWI, 30 min, 52–82%. d) BCl3, TBAI, DCM, 0 °C to room temperature, 6 h.
