Reaction SMILES: [CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][O:10][C@H:11]([C@@H:13]([C@@H:19]([O:22][CH2:23][CH2:24][CH3:25])[CH:20]=[CH2:21])[CH2:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH3:12])=[CH:5][CH:4]=1.B1C2CCCC1CCC2.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br/[CH:44]=[C:45](\[NH:56][C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])/[C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47]>C1COCC1.CN(C=O)C.O.Cl[Pd]Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:60]([O:59][C:57]([NH:56]/[C:45](=[CH:44]\[CH2:21][CH2:20][C@H:19]([O:22][CH2:23][CH2:24][CH3:25])[C@H:13]([C@@H:11]([O:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH3:12])[CH2:14][CH2:15][CH:16]([CH3:17])[CH3:18])/[C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47])=[O:58])([CH3:63])([CH3:62])[CH3:61]
Reactant: C=C[C@H](OCCC)[C@@H](CCC(C)C)[C@H](C)OCc1ccc(OC)cc1
Reactant: CC(C)(C)OC(=O)N/C(=C\Br)C(=O)OCc1ccccc1
Agent: Cl[Pd]Cl
Agent: [Fe+2]
Agent: B1C2CCCC1CCC2
Solvent: C1CCOC1
Solvent: O
Solvent: CN(C)C=O
Product: CCCO[C@@H](CC/C=C(\NC(=O)OC(C)(C)C)C(=O)OCc1ccccc1)[C@@H](CCC(C)C)[C@H](C)OCc1ccc(OC)cc1
Temperature: 25 °C
Reaction time: 6 h
Yield: 66.8 %

Procedure:
To a solution of 1-methoxy-4-((((2S,3S)-6-methyl-3-((S)-1-propoxyallyl)heptan-2-yl)oxy)methyl)benzene (1.25 g, 3.59 mmol) in THF (3 mL) was added 9-BBN (10.8 mL, 5.38 mmol, 0.5 M in THF) dropwise, and the reaction was stirred at room temperature for 6 h. The reaction mixture was carefully treated with an aq. solution of K3PO4 (3 M, 2.152 mL, 6.46 mmol; gas evolution), followed by a solution of (Z)-benzyl 3-bromo-2-((tert-butoxycarbonyl)amino)acrylate (1.30 g, 3.66 mmol) in DMF (3.59 mL), and PdCl2-dppf (0.262 g, 0.359 mmol). The reaction vessel was fitted with an air condenser and slowly warmed to 55° C. The solution became homogeneous and bright orange after 30 min. The reaction was maintained at this temperature for 20 h, at which point the color had turned a very dark red (almost black). The reaction was cooled to room temperature, diluted with H2O (30 mL), and the phases were separated. The aq. phase was extracted with Et2O (3×50 mL), and the combined organics were washed with brine (15 mL), dried over Na2SO4, filtered, and the filtrate was treated with Celite® (2 scoopula tip-fulls). The solvent was removed under reduced pressure and the resulting adsorbed material was directly loaded onto a column and purified using flash column chromatography (80 g SiO2, 0→25% acetone/hexanes) to afford the title compound (1.50 g, 2.397 mmol, 67%) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 7.40-7.29 (m, 5H), 7.25-7.20 (m, 2H), 6.88-6.80 (m, 2H), 6.59 (app t, J=7.5 Hz, 1H), 6.15 (s, 1H), 5.20 (app d, J=2.2 Hz, 2H), 4.48 (d, J=11.4 Hz, 1H), 4.34 (d, J=11.4 Hz, 1H), 3.78 (s, 3H), 3.57 (p, J=6.2 Hz, 1H), 3.36 (ddd, J=7.3, 5.3, 3.7 Hz, 1H), 3.33-3.19 (m, 2H), 2.36-2.16 (m, 2H), 1.72-1.38 (m, 16H), 1.38-1.13 (m, 6H), 0.91-0.82 (m, 9H); 13C NMR (101 MHz, CDCl3) δ 164.82, 158.99, 153.42, 137.06, 135.73, 131.13, 129.21, 128.52, 128.24, 128.22, 113.70, 80.33, 79.43, 74.78, 71.76, 69.86, 67.00, 55.25, 46.35, 38.73, 30.64, 28.68, 28.19, 25.39, 23.88, 23.47, 22.64, 22.61, 17.08, 10.79; ESIMS m/z 648 ([M+Na]+).