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Scheme for the synthesis of GS-βVG and β-deoxy-α-veratrylglycerone. Reagents and conditions were as follows: diethyl carbonate, NaH, THF, reflux, 2 h, 88% (i); DIBAL-H, THF, 2 h, 91% (ii); DDQ, 1,4-dioxane, 30 min, flash chromatography, 74% (iii); pyridinium tribromide, EtOAc, 30 min, flash chromatography, 27% (iv); glutathione, NaHCO3, 1:1 acetone/water, 14 h, 100% (v). See supplemental material for details.
