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Scheme for the synthesis of βGVE, GS-βVE, and β-guaiacyl-α-veratrylglycerone (β(R)GVG and β(S)GVG). Reagents and conditions were as follows: pyridinium tribromide, EtOAc, 30 min, 59% (i); guaiacol, K2CO3, acetone, 4 h, 82% (ii); glutathione, NaHCO3, 1:1 acetone/water, 14 h, 100% (iii); formaldehyde, K2CO3, 1,4-dioxane, 3 h, 88% (iv); chiral chromatography, ethanol/hexane (v). See supplemental material for details.
