Reaction Steps
95% TFA (3 mL) was added drop-wise to dimer compound 15j (210 mg, 0.19 mmol) at 0° C. This was then stirred for 1 hr and the mixture was poured into saturated NaHCO3 (30 mL) solution to naturalize the reaction mixture. The mixture was extracted with chloroform (3×20 mL). The organic layer was then washed water (20 mL), brine (20 mL) then dried (MgSO4) and filtrated. The excess solvent was removed under reduced pressure to give the crude product, which was subjected to flash column chromatography (SiO2, 2% methanol-chloroform). Removal of excess eluent under reduced pressure without heating afforded the final product 16j (112 mg, 0.17 mmol, 89%) as a solid: [α]20D=+637° (c=0.13, CHCl3); 1H NMR (CDCl3, 400 MHz): δ 1.24-1.51 (m, 16H, 14-H, 14′-H, 15-H, 15′-H, 16-H, 16′-H, 17-H; 17′-H); 1.78-1.93 (m, 4H, 13-H, 13′-H), 1.98-2.11 (m, 4H, 2-H, 2′-H), 2.25-2.38 (m, 4H, 1-H, 1′-H), 3.54-3.64 (m, 2H, 3-H, 3′-H), 3.68-3.76 (m, 2H, 11a-H, 11a′-H), 3.77-3.89 (m, 2H, 3-H, 3′-H), 3.93 (s, 6H, 7-OMe, 7′-OMe), 3.98-4.14 (m, 4H, 12-H, 12′-H), 6.79 (s, 2H, 9-H, 9′-H), 7.50 (s, 2H, 6-H, 6′-H), 7.64 (d, 2H, J=4.4, 11-H, 11′-H); 13C NMR (CDCl3, 400 MHz): δ 24.1, 25.9, 28.9, 29.3, 29.5, 29.5, 29.6, 46.6, 53.7, 56.1, 69.1, 110.4, 111.5, 120.0, 140.6, 147.8, 150.9, 162.3, 164.6; IR (neat): 3338, 2926, 1599, 1506, 1456, 1431, 1381, 1261, 1216, 1092, 1023 cm−1; MS (FAB) m/z (relative intensity) 723 ([M+2×MeOH]+., 9), 691 ([M+MeOH]+., 15), 659 (M+., 100).
