Water → HCID 68857440, compound

Participants

Reaction Steps

The allylsilane of Example 25 (0.15 g, 1 mmol, 1 eq.) was added to a stirring solution of NMO.H2O (0.4 g, 3 mmol, 3 eq.) and OsO4 (20 μL, 0.05 mmol, 0.05 eq.) in DCM (50 mL) and the reaction stirred overnight at room temperature. Na2SO3 (0.1 g) was added and the organic layer was washed with H2O (50 mL) and brine (50 mL), dried over MgSO4 and the solvent removed in vacuo. Column chromatography (cyclohexane:EtOAc, 60:40, RF=0.25) furnished the product as a colourless oil (0.1 g, 0.54 mmol, 54% yield); 1H NMR (400 MHz, CDCl3) 5.56 (1H, m, H-3), 5.50 (1H, m, H-4), 3.94 (1H, m, H-7), 3.81 (1H, m, H-6), 2.35 (1H, m, H-5), 1.86 (1H, m, H-5′), 1.86 (1H, m, H-2), 0.07 (9H, s, H-1); 13C NMR (100 MHz, CDCl3) δ 125.19 (C-4), 120.82 (C-3), 70.39 (C-6), 68.30 (C-7), 35.73 (C-2), 30.16 (C-5), −2.42 (C-1); IR (neat, cm−1) 3423 (b, OH) 1640 (b, C═C) MS (ESI-, m/z) 185.25 [M−H+].

Provenance & Evidence