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7.4 Hz, 1H), 4.00 (d, J = 14.4 Hz, 1H), 3.72 (s, 3H), 3.60 (dd, J = 17.7, 4.6 Hz, 1H), 3.57 (d, J =
14.4 Hz, 1H), 3.40-3.35 (m, 1H), 3.28-3.10 (m, 3H), 2.34-2.22 (m, 2H), 2.17-2.09 (m, 1H), 1.94-
1.81 (m, 2H), 1.75-1.60 (m, 2H), 0.98 (d, J = 6.7 Hz, 6H), 0.53 (t, J = 7.5 Hz, 3H); 13 C NMR (75
MHz, CDCl3): δ 179.0, 177.7, 171.5, 171.4, 166.5, 154.9, 143.5, 138.1, 132.7, 131.3, 130.0,
129.2, 128.9, 128.4, 126.9, 126.2, 66.9, 52.1, 48.0, 45.3, 44.2, 42.5, 41.6, 41.1, 28.5, 25.2, 20.9,
20.2, 20.2, 19.4, 12.6; IR (thin film): ν 3305, 2958, 1748, 1704, 1637 cm -1 ; HRMS calcd. for
C23H24N3O6 [M-190] + m/z 438.1665, found 438.1675.
Note: Fragment with m/z = 438 likely results from loss of a benzyl group and the CONH-i-Bu
fragment.
All
O
O
NH
O
N
H
NH
Bn
O
N
9-Benzyl-6-ethyl-2-methyl-1,3,7-trioxo-2,3,3a,4,5,9,9a,9b-octahydro-1H,7H-pyrrolo[3,4-
h]isoquinoline-8,9-dicarboxylic acid 8-allylamide 9-(isobutylamide) (163b). Allylamine (18
µL, 250 µmol) was added to a solution of 161b (12 mg, 25 µmol) in CHCl3 (1 mL) and the
reaction was stirred at rt for 1.5 h. The reaction mixture was diluted with CHCl3 and washed with
sat’d aq. NH4Cl. The organic layer was separated, dried over MgSO4 and concentrated under
vacuum. The crude residue was purified by flash chromatography (EtOAc : hexanes, 1 : 1 to 1 :
0, v/v) to give 163b (12 mg, 92%).
1 H NMR (300 MHz, CDCl3): δ 9.19 (t, J = 5.6 Hz, 1H), 7.90 (dd, J = 6.6, 3.9 Hz, 1H), 7.21-7.11
(m, 3H), 7.04-7.01 (m, 2H), 6.04-5.90 (m, 1H), 5.33 (dq, J = 17.2, 1.5 Hz, 1H), 5.20 (dq, J =
10.2, 1.4 Hz, 1H), 4.17-4.08 (m, 1H), 4.02 (d, J = 14.4 Hz, 1H), 3.99-3.90 (m, 1H), 3.54 (d, J =
218
163b
O