Reaction Steps
Diisobutylaluminum hydride (1.0 M in CH2Cl2, 23.3 mmol) was added dropwise to a 20° C. solution of natural product UK-2A (1) (5.8 imol, 3.0 g) in CH2Cl2 (60 mL). The mixture was stirred an additional 15 min and quenched with EtOAc (10 mL). Hydrochloric acid (2N, 100 mL) was added slowly and stirred vigorously for 15 min. The layers were separated and the organic layer dried (MgSO4) and concentrated in vacuo to give 1.82 g (70%) of 3 as a foamy, light yellow solid. 1H NMR (300 MHz, CDCl3): δ 11.82 (s, 1H), 8.63 (d, J=8.2 Hz, 1H), 8.01 (d, J=5.2 Hz, 1H), 7.32-7.20 (m, 5H), 6.89 (d, J=5.2 Hz), 5.35 (m, 1H), 5.16 (m, 1H), 4.86 (m, 1H), 3.96 (s, 3H), 3.76 (t, J=9.4 Hz, 1H), 3.62 (m, 1H), 3.25 (m, 1H), 3.02 (m, 1H), 2.77 (m, 1), 1.51 (d, J=6.3 Hz, 3H); 13C NMR (MHz, CDCl3): δ 173.2, 170.2, 169.4, 155.8, 149.2, 141.1, 138.8, 130.3, 129.2, 129.0, 127.0, 110.1, 77.6, 77.2, 65.4, 56.5, 54.4, 50.3, 35.4, 18.7 ppm; IR (KBr pellet): 3370 (br), 2966, 1751, 1654, 1529, 1453, 1263, 1045, 801 cm−1; Exact Mass: n/z calcd. for C22H24N2O8 [M]+=444.1533, found 444.1513.
