Reaction SMILES: [Si:1]([O:8][C@H:9]([C@H:13]([CH3:37])/[CH:14]=[CH:15]/[CH2:16][O:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:10][CH2:11][OH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.CC(=CC)C.[O-]Cl=O.[Na+].Cl.[CH3:55][NH:56][O:57][CH3:58].C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CS(C)=O.CCOCC.C1COCC1.O.Cl.CN(C1C=CN=CC=1)C>[Si:1]([O:8][C@H:9]([C@H:13]([CH3:37])/[CH:14]=[CH:15]/[CH2:16][O:17][C:18]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:10][C:11]([N:56]([O:57][CH3:58])[CH3:55])=[O:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
Reactant: C[C@H](/C=C/COC(c1ccccc1)(c1ccccc1)c1ccccc1)[C@H](CCO)O[Si](C)(C)C(C)(C)C
Reactant: CNOC
Agent: C(=NC1CCCCC1)=NC1CCCCC1
Agent: CC=C(C)C
Agent: CN(C)c1ccncc1
Solvent: CCN(CC)CC
Solvent: CS(C)=O
Solvent: O
Product: CON(C)C(=O)C[C@H](O[Si](C)(C)C(C)(C)C)[C@H](C)/C=C/COC(c1ccccc1)(c1ccccc1)c1ccccc1
Temperature: 25 °C
Reaction time: 1 h
Yield: 73.2 %

Procedure:
Sulfur trioxide pyridine complex (3.02 g, 19.1 mmol) was added to a stirred solution of alcohol 13 (3.26 g, 6.31 mmol) and triethylamine (2.6 mL, 19.1 mmol) in anhydrous CH2Cl2 (6 mL) and DMSO (12 mL) at 0° C. The reaction mixture was stirred at the ambient temperature for 1 h. The mixture was diluted with Et2O (100 mL) and washed with aqueous 0.5 N HCl (50 mL) and brine (10 mL). The separated organic layer was dried over MgSO4. Filtration and concentration followed by short flash column chromatography (hexane/EtOAc 4:1) provided the crude aldehyde as a colorless oil, which was used without further purification. A solution of the aldehyde in THF (25 mL) and H2O (12 mL) was treated with 2-methyl-2-butene in THF (2M, 18 mL, 9.0 mmol), NaH2PO4.H2O (2.6 g, 18.8 mmol) and NaClO2 (2.1 g, 18.6 mmol). The reaction mixture was stirred for 2 h, diluted with 1N HCl (20 mL) and extracted with CH2Cl2 (2×40 mL). The combined organic layers were dried over MgSO4, concentrated in vacuo and the crude acid was used for the next reaction without further purification. N,O-Dimethylhydroxylamine hydrochloride (0.62 g, 6.36 mmol), Et3N (0.88 mL, 6.31 mmol), DMAP (0.63 mmol) were successively added to a solution of the crude acid in CH2Cl2 (10 mL). The reaction mixture was cooled to 0° C. and DCC (1.30 g, 6.30 mmol) was added. The mixture was stirred at ambient temperature for 15 h and filtered. The filtrate was washed with 0.5 N HCl, saturated aqueous NaHCO3, and brine, dried over anhydrous MgSO4 and concentrated. Purification by column chromatography over silica gel (hexane/EtOAc 4:1) gave the Weinreb amide 15 (2.65 g, 73% for 3 steps) as a colorless oil: IR (CHCl3) 2956, 2929, 2855, 1663, 1448, 1252, 1083, 1032, 836 cm−1; 1H NMR (300 MHz, CDCl3) ε7.58 m, 6H), 7.37 (m, 9H), 5.89 (dd, J=15.6, 7.6 Hz, 1H), 5.72 (dt, J=15.6, 5.2 Hz, 1H), 4.38 (ddd, J=8.0, 5.0, 3.0 Hz, 1H), 3.74 (s, 3H), 3.70 (d, J=5.1 Hz, 2H), 3.27 (s, 3H), 2.79 (dd, J=15.1, 7.4 Hz, 1H), 2.52 (m, 2H), 1.20 (d, J=6.9 Hz, 3H), 1.02 (s, 9H), 0.22 (s, 3H), 0.16 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 172.6, 144.2, 133.3, 128.5, 127.7, 127.5, 126.8, 86.7, 72.4, 64.8, 61.2, 42.4, 36.3, 31.9, 25.8, 18.0, 15.7, −4.6, −5.0; LRMS (ESI) 596.2 [M+Na]+, 449.2, 243.0; HRMS (ESI) calcd for C35H47O4NSiNa 596.3172 [M+Na]+, found 596.3165; [α]20D−14.7 (c 0.65 , CHCl3).