C([O:8][C:9](=[O:35])[CH2:10][CH:11]([S:19]([N:22]1[CH2:27][CH2:26][CH:25]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:24][CH2:23]1)(=[O:21])=[O:20])[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)C1C=CC=CC=1>CCOC(C)=O.[Pd]>[CH2:28]([CH:25]1[CH2:26][CH2:27][N:22]([S:19]([CH:11]([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:10][C:9]([OH:35])=[O:8])(=[O:21])=[O:20])[CH2:23][CH2:24]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1The product from Step E (360 mg, 0.73 mmol) was taken up in EtOAc (10 mL) with stirring under a blanket of argon. 10% palladium on charcoal (130 mg) was added. The resulting suspension was hydrogenated in a PARR apparatus at room temperature overnight. The system was purged with argon and the catalyst removed by filtration. The filtrate was evaporated under reduced pressure to give the desired product as a gum (292mg, Quant). 1H-NMR δ(MeOD) 7.24-7.10 (10H, m), 3.89 (1H, m), 3.69 (2H, m), 3.25 (1H, dd, J=4.8, 17.1 Hz), 2.81-2.64 (4H, m), 2.53 (2H, d, J=6.7 Hz), 2.45 (1H, dd, J=4.8, 17.1 Hz), 1.61 (3H, m) and 1.28 (2H, m). 13C-NMR δ(MeOD) 174.3, 141.7, 138.8, 130.8, 130.6, 130.2, 129.7, 128.4, 127.4, 61.0, 47.6, 44.2, 39.2, 36.6, 34.8, 33.7. ESMS=(M+1) 402.2, (M−1) 400.0.
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