Reaction SMILES: [CH:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([CH3:30])[C:14]=1[O:15][C@H:16]1[C@@H:21]3[O:22]C(=O)[O:24][C@@H:20]3[C@@H:19]([O:26][CH3:27])[C:18]([CH3:29])([CH3:28])[O:17]1)[O:11][C:10](=[O:31])[C:9]([NH:32][C:33](=[O:42])OCC1C=CC=CC=1)=[CH:8]2)([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.[CH3:54][O:55][C:56]1[CH:57]=[C:58]([C:62]2[C:67]([O:68][CH3:69])=[CH:66][CH:65]=[C:64](C(O)=O)[CH:63]=2)[CH:59]=[CH:60][CH:61]=1.C(=O)([O-])[O-]>[Pd].C1COCC1.N1C=CC=CC=1.C(Cl)Cl.CO.C(Cl)Cl.C(N(CC)CC)C>[OH:22][C@@H:21]1[C@H:20]([OH:24])[C@@H:19]([O:26][CH3:27])[C:18]([CH3:28])([CH3:29])[O:17][C@H:16]1[O:15][C:14]1[C:13]([CH3:30])=[C:12]2[C:7]([CH:8]=[C:9]([NH:32][C:33]([C:64]3[CH:63]=[C:62]([C:58]4[CH:59]=[CH:60][CH:61]=[C:56]([O:55][CH3:54])[CH:57]=4)[C:67]([O:68][CH3:69])=[CH:66][CH:65]=3)=[O:42])[C:10](=[O:31])[O:11]2)=[CH:6][C:5]=1[O:4][CH:1]([CH3:3])[CH3:2]
Reactant: COc1cccc(-c2cc(C(=O)O)ccc2OC)c1
Reactant: CO[C@@H]1[C@H]2OC(=O)O[C@H]2[C@H](Oc2c(OC(C)C)cc3cc(NC(=O)OCc4ccccc4)c(=O)oc3c2C)OC1(C)C
Agent: [Pd]
Agent: CCN=C=NCCCN(C)C
Agent: O=C([O-])[O-]
Solvent: c1ccncc1
Solvent: CCN(CC)CC
Solvent: ClCCl
Product: COc1cccc(-c2cc(C(=O)Nc3cc4cc(OC(C)C)c(O[C@@H]5OC(C)(C)[C@H](OC)[C@@H](O)[C@H]5O)c(C)c4oc3=O)ccc2OC)c1
Reaction time: 12 h
Yield: 14.6 %

Procedure:
Palladium on carbon (10%, 11 mg) was added to 25c (54.5 mg, 0.093 mmol) in anhydrous THF (600 μL) and the solution was placed under an atmosphere of H2. After 12 hours, the solution was filtered through SiO2 (1:1 CH2Cl2:Acetone) and the eluent was concentrated to afford a yellow solid, which was used without further purification (42.0 mg, 99%). EDCI (14.9 mg, 0.078 mmol) and 3′,6-dimethoxybiphenyl-3-carboxylic acid (16 mg, 0.062 mmol) were added to the amine (14.0 mg, 0.031 mmol) in 30% pyridine/CH2Cl2 (900 μL). After 12 hours, the solvent was concentrated and the residue purified via column chromatography (SiO2, 3:1 Hexane:Ether→40:1 CH2Cl2:Acetone) to afford a colorless solid, which was used without further purification (17.5 mg, 82%). Triethylamine (150 μL) was added to the carbonate (17.5 mg, 0.025 mmol) in MeOH (2.50 mL) and CH2Cl2 (2.50 mL). After 12 hours, the solvent was concentrated and the residue purified via column chromatography (SiO2, 10:1 CH2Cl2:Acetone) to afford 26c as a colorless amorphous solid (6.0 mg, 35%, 28% over 3 steps): 1H NMR (CD2Cl2, 500 MHz) δ 8.69 (s, 1H), 8.67 (s, 1H), 7.84 (dd, J=8.6, 2.4 Hz, 1H), 7.80 (d, J=2.4 Hz, 1H), 7.29 (d, J=8.0 Hz, 1H), 7.25 (t, J=7.9 Hz, 1H), 7.03-7.01 (m, 2H), 6.87 (s, 1H), 6.87-6.83 (m, 1H), 4.96 (d, J=6.8 Hz, 1H), 4.61-4.56 (m, 1H), 4.19 (t, J=4.0 Hz, 1H), 3.89 (dd, J=6.8, 3.7 Hz, 1H), 3.82 (s, 3H), 3.76 (s, 3H), 3.75 (s, 1H), 3.41 (s, 3H), 3.34 (s, 1H), 3.03 (d, J=4.5 Hz, 1H), 2.36 (s, 3H), 1.33 (t, J=6.2 Hz, 6H), 1.25 (s, 3H), 1.23 (s, 3H); 13C NMR (CD2Cl2, 125 MHz) δ 164.6, 159.1, 158.6, 158.3, 146.7, 146.3, 142.5, 138.1, 130.2, 129.1, 128.3, 127.4, 125.2, 122.8, 122.2, 121.2, 121.1, 115.5, 144.5, 112.1, 110.2, 108.4, 101.4, 81.9, 77.0, 71.1, 69.2, 68.3, 59.1, 55.1, 54.5, 28.7, 28.6, 20.8, 20.8, 9.1; IR (film) νmax 2924, 2854, 2359, 2341, 1734, 1684, 1653, 1558, 1541, 1522, 1506, 1458, 1387, 1339, 1286, 1244, 1113, 912, 797 cm−1; HRMS (ESI+) m/z: [M+Na]+ calcd for C36H41NO11, 686.2578. found, 686.2610.