Reaction Steps
To a solution of alcohol 77 (183.6 mg, 0.599 mmol, 1.00 equiv) in 1:1 THF:H2O (9.2 mL) was added Hg(OAc)2 (382 mg, 1.199 mmol, 2.00 equiv). The resulting solution was stirred at 23° C. for 45 minutes. A 0.5M solution of NaBH4 in 3M NaOH (1.2 mL, 0.599 mmol, 1.00 equiv) was then added by syringe, resulting in an immediate precipitation of Hg0. After stirring for 5 minutes, the suspension was partitioned between 20 mL sat'd NH4Cl soln. and 20 mL EtOAc. The phases were separated and the aqueous phase was extracted with 2×20 mL EtOAc. The combined organic phases were dried over MgSO4 and solvent removal yielded a grey suspension that was purified by silica gel column chromatography (5:1 hex:EtOAc) to yield tetrahydrofuran S12 (141.6 mg, 77%) as a clear, colorless oil. Rf=0.58 (2:1 hex:EtOAc); 1H NMR (500 MHz, CDCl3) δ 7.34 (m, 5H, aryl H), 5.21 (d, 1H, J=12.3 Hz, PhCH2), 5.17 (d, 1H, J=12.3 Hz, PhCH2), 3.59 (s, 3H, OCH3), 2.91 (d, 1H, J=15.4 Hz, C(O)CH2), 2.81 (d, 1H, J=15.4 Hz, C(O)CH2), 2.41 (m, 1H, CH2), 2.16 (m, 1H, CH2), 1.85 (m, 1H, CH2), 1.78 (m, 1H, CH2), 1.30 (s, 3H, C(CH3)2), 1.24 (s, 3H, (CCH3)2); 13C NMR (125 MHz, CDCl3) δ 173.70, 170.54, 135.93, 128.59, 128.43, 128.32, 84.26, 83.96, 67.10, 51.80, 43.93, 37.88, 35.58, 29.09, 28.33; IR (neat film) 3036 (w), 2973 (m), 1743 (s), 1500 (w), 1458 (m), 1440 (m), 701 (m) cm−1; LRMS (ESI) calc'd for C17H22O5Na (M+Na+) 329.2; found 329.1.
