Experimental

Synthesis of Compound 28 from Compound 27: 1.05 g of compound (+)- 27 (2.85 mmol) was dissolved in 36 mL of THF. Then, N-methylmorpholine-N-oxide (500 mg, 4.227 mmol)and MeSO₂NH₂ (388 mg, 4.27 mmol) were added. Following this, OsO₄ was added (67 mL, 0.14 mmol, 0.5% dilution in water) via a syringe followed by 9 mL of H₂O. The reaction mxture was stirred at room temperature overnight before quenching with a saturated solution of Na2S2O3. The reaction mixture was then extracted with Ethyl acetate three times and the combined organic layers were dried over anydrous Na₂SO₄, filtered and concentrated. Flash chromotography (3:1 hexanes/Ethyl Acetate) resulted in compound(+)-28 (1.06 g, 2.63 mmol, 92% yield) as a white foam.

Synthesis of Compound 29 from Compound 28: A solution of 28 (1.02 g, 2.54 mmol) in 2,2-dimethoxypropane (10mL) and dichloromethane (10 mL) and p-toluenesulfonate (PPTS, 50 mg, 0.20 mmol) was added to a reaction flask. The reaction mixture was stirred at room temperature and monitored via TLC until the substrate 28 was fully converted. Then NaHCO₃ (180 mg) was added followed by 30 mL hexanes. The resulting suspension was filtered through Celite and then concentrated. Flash chromatography (10:1 hexanes/ Ethyl Acetate) resulting in (+)-29 (1.05 g, 2.37 mmol, 94%) as a white foam.