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40949146637
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To a solution of compound 3 (150 mg, 1.03 mmol) in anhyd MeCN (10 mL, NIS (278 mg, 1.23 mmol) was added and stirred for 3 d under inert atmosphere. The reaction mixture was extracted with Et2O, washed with brine, dried over Na2SO4, and concentrated in vacuo. The crude was purified via chromatography (SiO2, hexane-EtOAc, 30:1) to yield the desired compound 5 (34, Selected Spectral Data Compound 5: 1H NMR (200 MHz, CDCl3, δ, 3.35 (2 H, t, J, 4.0 Hz, CH2CH2O, 4.26 (2 H, t, J, 4.1 Hz, CH2CH2O, 5.64 (1 H, d, J, 8.4 Hz, ArCHCHOCH2, 6.54 (1 H, d, J, 8.4 Hz, ArCHCHOCH2, 7.28 (1 H, d, J, 8.3 Hz, ArH, 7.38 (1 H, d, J, 8.3 Hz, ArH, 13C NMR 50 MHz, CDCl3, δ, 43.02, 71.28, 100.68, 100.76, 108.71, 136.99, 138.08, 139.11
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2O].
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31
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40949160252
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To a solution of alcohol 6 (10 mg, 0.037 mmol) in CH 2Cl2 (5 mL, Ac2O (4 μL, 0.044 mmol, Et3N (6 μL, 0.044 mmol, and DMAP (5 mol, were added at 0°C. The reaction mixture was stirred for 10 min after which it was poured into H2O and CH2Cl2. The organic layer was washed with H2O, dried, and then evaporated. The compound 6a was then isolated by column chromatography (SiO2, hexane-EtOAc, 30:1) as a white solid (98, Selected Spectral Data Compound 6a: 1H NMR (400 MHz, CDCl3, δ, 2.14 (3 H, s, CH3COOCH, 2.94, 3.50 (2 H, ABX, JAX= 4.4 Hz, JBX, 0.0 Hz, JAB, 14.8 Hz, ArCH2CHOH, 5.87 (1 H, d, J, 4.0 Hz, ArCHOHCH2, 7.28 (1 H, d, J, 8.4 Hz, ArH, 7.36 1 H, d, J, 8.0 Hz, ArH, 13
-
+].
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