Reaction SMILES: C[CH:2]1[C:20](=[O:21])[O:19][CH:18]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:16](=[O:17])[O:15][CH:14]([CH:26]([CH:28]2[O:30][CH:29]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH3:27])[CH2:13][CH:12]=[CH:11][C:9](=[O:10])[NH:8][CH:7]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[C:40]([Cl:46])[CH:39]=2)[C:5](=[O:6])[NH:4][CH2:3]1.OC(C(C)C(O)C(O)C1C=CC=CC=1)CC=CC(O)=O.ClC1C=C(C=CC=1OC)C[C@@H](C(O)=O)N.NCCC(O)=O.C(O)(=O)C(CC(C)C)O.C[C@H]1C(=O)O[C@@H](CC(C)C)C(=O)O[C@H]([C@@H]([C@H]2O[C@@H]2C2C=CC=CC=2)C)CC=CC(=O)N[C@H](CC2C=CC(OC)=C(Cl)C=2)C(=O)NC1.C[C@H]1C(=O)O[C@@H](CC(C)C)C(=O)O[C@H]([C@@H](/C=C/C2C=CC=CC=2)C)CC=CC(=O)N[C@H](CC2C=CC(OC)=C(Cl)C=2)C(=O)NC1.C[C@H]1C(=O)O[C@@H](CC(C)C)C(=O)O[C@H]([C@@H](/C=C/C2C=CC=CC=2)C)CC=CC(=O)N[C@H](CC2C=CC(OC)=CC=2)C(=O)NC1.C[C@@H]1[C@@H](O)[C@H](C2C=CC=CC=2)O[C@H]1C/C=C/C(N[C@@H](C(NC[C@H](C(OC)=O)C)=O)CC1C=CC(OC)=C(Cl)C=1)=O>>[CH3:27][C@H:26]([C@H:28]1[O:30][C@@H:29]1[C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C@H:14]1[O:15][C:16](=[O:17])[C@H:18]([CH2:22][CH:23]([CH3:24])[CH3:25])[O:19][C:20](=[O:21])[CH2:2][CH2:3][NH:4][C:5](=[O:6])[C@@H:7]([CH2:37][C:38]2[CH:43]=[CH:42][C:41]([O:44][CH3:45])=[C:40]([Cl:46])[CH:39]=2)[NH:8][C:9](=[O:10])[CH:11]=[CH:12][CH2:13]1
Reactant: COc1ccc(CC2NC(=O)C=CCC(C(C)C3OC3c3ccccc3)OC(=O)C(CC(C)C)OC(=O)C(C)CNC2=O)cc1Cl
Agent: CC(C(O)CC=CC(=O)O)C(O)C(O)c1ccccc1
Agent: CC(C)CC(O)C(=O)O
Agent: COC(=O)[C@H](C)CNC(=O)[C@@H](Cc1ccc(OC)c(Cl)c1)NC(=O)/C=C/C[C@@H]1O[C@@H](c2ccccc2)[C@H](O)[C@H]1C
Product: COc1ccc(C[C@H]2NC(=O)C=CC[C@@H]([C@H](C)[C@H]3O[C@@H]3c3ccccc3)OC(=O)[C@H](CC(C)C)OC(=O)CCNC2=O)cc1Cl

Procedure:
[α]D +40.2° (CHC13 c 0.72); UV λmax (ε) 240 (6700), 280 (2400), 288 (2100); IR (neat) νmax 3403, 3279, 2957, 1731, 1673, 1503, 1464, 1409, 1372, 1258, 1174, 1065, 1023, 889 cm-1 ; EIMS m/z (relative intensity) 640/642 (10/4), 612 (5), 478 (15), 398 (40), 266 (33), 227 (76), 195 (95), 155 (100), 127 (90); high resolution EIMS m/z 640.2550 (calcd for C34H41ClN2O8, 0.2 mmu error); 1H NMR (CDCl3) amino or hydroxy acid unit δ (carbon positions, multiplicities; J in Hz) 7,8-epoxy-5-hydroxy-6-methyl-8-phenyl octanoic acid (A) 5.73 (2, d; 15.4), 6.68 (3, ddd; 15.0, 9.9 and 4.9), 2.45 (4, m), 2.56 (4, m), 5.19 (5, ddd; 11.2, 5.1 and 1.5), 1.80 (6, m), 1.14 (6-Me, d; 7.1), 2.92 (7, dd; 7.5 and 2.0), 3.68 (8, d; 1.8), 7.25 (10/14, m), 7.33-7.38 (11/12/13, m); 3-chloro-4-methoxyphenylalanine (B )4.74 (2, ddd; 8.2, 6.8 and 6.2), 5.68 (2-NH, d; 8.6), 2.98 (3, dd; 14.3 and 7.7), 3.14 (3, dd; 14.3 and 5.6), 7.21 (5, d; 2.0), 3.86 (7-OMe, s), 6.83 (8, d; 8.4), 7.07 (9, dd; 8.4 and 2.0), 3-aminopropionic acid (C )2.56 (2, m), 3.51 (3, m), 3.45 (3, m), 6.90 (3-NH, br t; 5.8); leucic acid (D )4.89 (2, dd; 10.0 and 3.3), 1.67 (3, m), 1.31 (3, m), 1.67 (4, m), 0.84 (5, d; 6.4), 0.83 (5', d; 6.4); 13C NMR (CDCl3) unit δ (carbon position) A 165.5 (1), 125.3 (2), 141.0 (3), 36.7 (4), 75.9 (5), 40.6 (6), 13.5 (6-Me), 63.0 (7), 59.0 (8), 136.7 (9), 125.6 (10/14), 128.7 (11/13), 128.5 (12); B 170.7 (1), 53.9 (2), 35.0 (3), 129.8 (4), 130.9 (5), 122.4 (6), 153.9 (7), 56.1 (7-OMe), 112.2 (8), 128.3 (9); C 172.6 (1), 32.4 (2), 34.4 (3), D 170.5 (1), 71.2 (2), 39.5 (3), 24.4 (4), 22.8 (5), 21.2 (5').