Synthesis of 17: 800 mg of compound (+)-11 (2.88 mmol), 437 mg of K2CO3 (3.16 mmol, 1.1 equiv.), and 985 microL of MeI (15.8 mmol) were combined in a solution of 15 mL of Acetone and stirred for 6 hours at 22°C.
After this, 20 mL of aqueous 2M NaOH was added and stirred for an additional 30 minutes. Then aqueous 2M HCl was added, and the aqueous layer was extracted 4 times with CH2Cl2.
The combined organic layers were then dried with Na2SO4, filtered, and then concentrated by vacuum. The product was then purified via flash column chromatography with a solvent ratio hexanes/acetone = 4:1.
This produced 4476 mg (62%) of the target molecule (-)-17 as a white foam, and 110 mg (14%) of its epimer, epi-17, also as a white foam. The total yield was 76% with a diastereomeric ratio of 4.4:1.
