Reaction Steps
PdCl2 (40 mg) was added to a solution of the allyl ether (24) (1.09 g, 0.97 mmol) in MeOH (10 mL) and 1,2-DCE (10 mL) and the combined mixture was heated (70°, 40 min). After the time, the solvents were evaporated and the residue subjected to FC (20-30% EtOAc/hexanes) to yield the alcohol (25) as a colourless oil (0.96 g, 91%). 1H NMR (CDCl3) δ 3.68-3.81, 3.97-4.06, 4.32-4.71 (3 m, 18 H; H-2I,-3I,-4I,-5I,-6aI,-6bI,-3II,-5II,-6aII,-6bII, CH2Ph), 4.84 (d, 1 H, JA,B 12 Hz; A of AB quartet), 5.05 (d, 1 H, J1,2 1.9 Hz; H-1I), 5.26 (d, 1 H; J1,2 1.9 Ha; H-1II), 5.61 (dd, 1 H, J2,3 3.3 Hz; H-2II), 5.67 (dd, 1 H, J3,4 9.8, J4,5 9.9 Hz; H-4II), 7.13-7.40, 7.48-7.59, 7.98-8.06 (3 m, 35 H; Ar). 13C NMR (CDCl3) δ 60.61, 63.32 (2C; C-6I,-6II), 69.06, 69.12, 69.25, 69.44, 70.45, 72.14, 72.65, 72.77, 73.48, 74.79, 75.48, 75.47, 76.23 (13C; C-3I,-4I,-5I,-2II,-3II,-4II,-5II, OCH2, CH2Ph), 79.66(C-2I), 98.34, 99.40 (C-1I,-1II), 127.70-138.47 (42C; Ar), 165.97, 166.36, 166.97 (3C; C═O).
