Reaction Steps
Compound 185 (0.70 g, 1.17 mmol) was dissolved in dry methanol. The reaction was cooled to 0° C. and NH3 in MeOH (1.5 ml, Ca. 9 M) was added dropwise via syringe. The reaction mixture was allowed to warm gradually to room temperature. After stirring for 24 hours the solution was concentrated to dryness, and the residue was chromatographed on a silica gel column with EtOAc/Hexane (6:4-8:2) as eluent to give 186 (0.40 g, 61%). 1H NMR (CDCl3): δ8.68 (br, 1 H, NH), 7.61 (m, 1 H, Tr), 7.43 (d, 1 H, J=1.1 Hz, H-6), 7.33-7.28 (m, 9 H, Tr), 6.85-6.82 (m, 4 H, Tr), 6.14 (dd, 1 H, J=4.7, 6.7 Hz, H-1'), 3.99-3.97 (m, 1 H, H-4'), 3.79 (s, 6 H, OCH3), 3.64-3.61 (m, 2 H, CH2OH), 3.51 (dd, 2 H, J=3,6, 10.5 Hz, H-5') 3.36 (dd, 1H, J=3.6, 10.5 Hz, H-5"), 2.62-2.60 (m, 1 H, H-3'), 2.35-2.31 (m, 1 H, H-2'), 2.24-2.20 (m, 1 H, H-2"), 2.12 (m, 1 H, OH), 2.05 (s, 3 H, COCH3), 1.52 (s, 3 H, CH3); 13C NMR (CDCl3): 163.7 (C4), 158.6, 150.3 (C2), 144.3, 135.7 (C6), 135.4, 130.1, 128.0 & 127.9 (d), 127.1, 113.2, 110.7 (C5), 86.9, 85.1 (C1'), 82.3 (C4'), 64.1 (C5'), 63.1, 55.2, 41.5 (C3'), 32.8 (C2'), 12.0.
