Reaction SMILES: Br[CH2:2][CH2:3][CH2:4][C:5]([CH3:15])([CH3:14])[CH2:6][O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1.[C:16]1([CH3:28])[CH:21]=[CH:20][C:19]([S:22]([CH2:25][N+:26]#[C-:27])(=[O:24])=[O:23])=[CH:18][CH:17]=1.[H-].[Na+]>CS(C)=O.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl.O>[N+:26]([C:25]([S:22]([C:19]1[CH:18]=[CH:17][C:16]([CH3:28])=[CH:21][CH:20]=1)(=[O:23])=[O:24])([CH2:2][CH2:3][CH2:4][C:5]([CH3:14])([CH3:15])[CH2:6][O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1)[CH2:2][CH2:3][CH2:4][C:5]([CH3:15])([CH3:14])[CH2:6][O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1)#[C-:27]
Reactant: CC(C)(CCCBr)COC1CCCCO1
Reactant: [C-]#[N+]CS(=O)(=O)c1ccc(C)cc1
Agent: CCCC[N+](CCCC)(CCCC)CCCC
Agent: [H-]
Agent: [I-]
Solvent: O
Solvent: ClCCl
Solvent: CS(C)=O
Product: [C-]#[N+]C(CCCC(C)(C)COC1CCCCO1)(CCCC(C)(C)COC1CCCCO1)S(=O)(=O)c1ccc(C)cc1
Temperature: 25 °C
Reaction time: 6 h
Yield: 113.2 %

Procedure:
Under N2 atmosphere, to a solution of 5-bromo-1-(tetrahydropyranyloxy)-2,2-dimethylpentane (40.0 g, 0.143 mol) and p-toluenesulphonylmethyl isocyanide (TosMIC; 13.99 g, 0.072 mol) in anhydrous DMSO (400 mL) was added sodium hydride (60% dispersion in mineral oil, 6.86 g, 0.173 mol) under cooling in a water-bath. Tetra-n-butylammonium iodide (5.28 g, 0.0143 mol) was then added while cooling in a water-bath. The mixture was stirred for 6 h at rt., then carefully hydrolyzed by drop-wise addition of water (100 mL) under cooling in a water-bath. The reaction mixture was diluted with dichloromethane (100 mL), additional water (100 mL), and dichloromethane (100 mL). The layers were separated and the aqueous layer was extracted with dichloromethane (3×100 mL). The combined organic layers were washed with water (2×200 mL) and saturated NaCl solution (100 mL), dried over MgSO4, concentrated in vacuo, and dried in high vacuo to give crude 2-[6-isocyano-2,2,10,10-tetramethyl-11-(tetrahydropyran-2-yloxy)-6-(toluene-4-sulfonyl)-undecyloxy]-tetrahydropyran (47.9 g) as a brownish, viscous oil. This crude oil (47.0 g) was dissolved in methanol (200 mL) and water (40 mL). Concentrated sulfuric acid (20 mL) was added drop-wise over 10 min whereupon the solution warmed up to ca. 30° C. The reaction mixture was stirred at rt for ca. 150 min and then diluted with water (200 mL). The mixture was extracted with CH2Cl2 (2×200 mL, 1×100 mL) and the combined organic layers were washed with water (200 mL), 10% potassium hydroxide solution (3×200 mL), water (200 mL), and brine (160 mL). The organic extracts were dried over MgSO4, concentrated in vacuo, and dried in high vacuo to furnish crude 1,11-dihydroxy-2,2,10,10-tetramethyl-undecan-6-one (26.0 g) as a brown oil. The crude product was purified by chromatography (silica, 330 g, hexanes/ethyl acetate=90/10, 70/30, 50/50) to obtain three fractions: A: 1.1 g, 93.5% purity by HPLC, 5.6% yield; B: 3.0 g, ca. 96.7% purity by HPLC, 16% yield, and C: 4.0 g, ≧90% purity by NMR, 19.5%. Fraction C was again purified by chromatography (silica, 150 g, hexanes/ethyl acetate=60/40) to give clean product (1.5 g, purity by HPLC: 96.3%). Overall yield: 5.6 g, 30.3% over two steps. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm) 3.25 (s, 4H), 2.60 (br., 2H), 2.32 (t, 4H, J=7.2), 1.45 (m, 4H), 1.12 (m, 4H), 0.79 (s, 12H). 13C NMR (75 MHz, CDCl3=77.0 ppm/TMS): δ (ppm) 212.25, 70.99, 43.15, 37.69, 34.94, 23.89, 17.91. HRMS (LSIMS, gly): Calc for C15H29O2 (MH+—H2O): 241.2168, found: 241.2169.