Experimental

          5.900g (16.51mmol, 2.00eq) of PhNTf₂ was added to a 500mL flask fitted with a stir bar. To this, 165mL of THF was dissolved and the solution was cooled to 0 °C. The dried solution of molecule (+)-17 (2.380g, 8.252mmol, 1.00eq.) was dissolved in 24mL of THF and added to the PhNTf₂ solution. Immediately after, 31mL of 0.4M KHMDS solution (12.4mmol, 1.50eq.) in THF was added to the reaction mixture. After 1 hour of stirring at 0 °C, the reaction mixture was quenched with 300mL of aqueous, saturated NaHCO3 solution at 0 °C in an Erlenmeyer flask). The reaction mixture was then transferred to a 2L separatory funnel, diluted with 300mL of hexanes, and washed four times each with 300mL of aqueous KOH (3M). The organic layer was extracted and washed with H2O two times each with 400mL, then with brine two times each with 400mL. The resulting organic layer was dried with MgSO₄ and evaporated, in a vacuum, with a 500mL round-bottom flask.

          The product was dissolved in 83mL of THF and cooled to 0 °C. 477mg of Pd(PPh₃)₄ (0.413mmol, 0.05 eq.) was dissolved in 19mL of THF and added to the product solution. The resulting solution was stirred for 5 minutes at 0 °C. After, 34mL of 1.2M solution of Me₂Zn in PhMe (40.8mmol, 4.94 eq.) was added, and the solution was stirred for 5 minutes at 0 °C. Once the ice bath was removed, the reaction mixture was warmed to room temperature over 5 hours. The solution was quenched with 100mL of 1M HCl and extracted by washing twice with hexanes with 200mL each time. The organic layer was then washed with 30mL of H₂O and then with 30mL of brine. The resulting organic solution was dried with MgSO₄ and evaporated in a vacuum. The desired product was purified using silica gel flash chromatography (gradient of EtOAc/hexanes) and crystallized in hot MeOH. 1.9745g (83.5% yield) was obtained.

Glossary

Separatory Funnel: A glass, laboratory equipment used in liquid-liquid extraction, where compounds can be isolated by their differences in solubility. For example, water and most organic solvents are immiscible, which allows ionic compounds to selectively dissolve in water while the covalent compounds selectively dissolve in the organic solvent.

Flash Chromatography: A method to purify compounds. Chemical compounds are run through a stationary phase, usually silica, with a developing solvent. Positive pressure is used to expedite this process. The differences in hydrogen-bonding ability of the compounds allow the compounds to elute out of the column at different rates, thereby allowing them to be isolated in relative purity.

Recrystallization (from "crystallized"): A method used to purify solid compounds that utilize the solubility differences of a solvent caused by altering temperature. Specifically, a saturated solution is created by dissolving a compound, that ideally has insoluble impurities, into a small amount of heated solvent. Then the solvent is allowed too cool, whereby the compound desired forms crystals but the impurities stay in solution. The resulting mixture can be filtered to isolate the desired product in high purity.