Syntheses of Diarylheptanoids and 3-Substituted Isocoumarins

All reactions were carried out in oven dried glass wares. Reactions requiring inert atmosphere were carried out under nitrogen atmosphere. Dry THF was distilled as needed from Na/benzophenone ketyl. All anhydrous solvents were prepared according to standard procedures. Solvents used for chromatography were LR grade. Thin-layer chromatography was performed on aluminum plates coated with silica gel 60. Visualization was observed by UV light irradiation or by dipping into (Hanessian?s stain) a solution of cerium (IV) sulfate (2.5 g) and ammonium molybdate (6.25 g) in 10% sulfuric acid (250 mL) followed by charring on a hot plate. For olefins, permanganate stain was used (3 g potassium permanganate, 20 g potassium carbonate, 5 mL 5% sodium hydroxide, 300 mL water). For aldehydes, 2,4-DNP stain prepared by dissolving 6 g of 2, 4-dinitrophenylhydrazine in 30 mL of sulfuric acid and 40 mL of water in 100 mL of 95% ethanol was used.