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61949235892
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Spectroscopic data of 3: 1H NMR (400 MHz, CDCl 3, δ, 7.35-7.31 (m, 2H, furyl-5, furyl-2, 6.43 (s br, 1H, furyl-4, 2.91-2.82 (m, 2H, H-5ax, H-3 a,ax, 2.15-2.06 (m, 1H, H-8a,ax, 1.97-1.89 (m, 1H, H-8eq, 1.88-1.75 (m, 2H, H-3b,eq, H-6a,ax, 1.71-1.53 (m, 6H, H-7a,b, H-1a,b H-2a,b, 1.52-1.45 (m, 1H, H-6b,eq, 1.04 ppm (d, 3J, 7.0, 3H, CH3, 13C NMR (100.6 MHz, CDCl3, δ, 142.58 (furyl-5, 139.06 (furyl-2, 128.70 (furyl-3, 109.71 (furyl-4, 67.54 (C-8a, 60.91 (C-5, 53.40 (C-3, 32.14 (C-1, 29.42 (C-8, 28.92 (C-6, 26.84 (C-7, 20.06 (C-2, 12.19 ppm (CH3, ESI-MS (pos, 206.16, M+H, calcd. 206.15, HR ESI-MS pos, 206.1552, M+H, calcd. 206.1545
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+, calcd. 206.1545).
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30
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61949473264
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Addition of the protonating reagent at -95°C increased the diastereomeric ratio to 93:7.
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Addition of the protonating reagent at -95°C increased the diastereomeric ratio to 93:7.
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31
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61949112170
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Spectroscopic data of 4: 1H NMR (400 MHz, CDCl 3, δ, 7.35 (m, 2H, furyl-5, furyl-2, 6.47 (sbr, 1H, furyl-4, 2.99-2.78 (m, 2H, H-3a, H-5, 2.01-1.90 (m, 2H, H-1a, H-3b, 1.84-1.70 (m, 3H, H-7a, H-6 a,b, 1.68-1.55 (m, 3H, H-2a,b, H-8a, 1.54-1.36 (m, 2H, H-1b, H-8, 1.14-1.01 (m, 1H, H-7b, 0.91 (d, 3J, 6.5, 3H, CH3, 13C NMR (100.6 MHz, CDCl3, 142.75 (furyl-5, 139.38 (furyl-2, 128.01 (furyl-3, 109.73 (furyl-4, 71.50 (C-8a, 59.81 (C-5, 53.09 (C-3, 36.25 (C-8, 33.99 (C-6, 33.83 (C-7, 28.97 (C-1, 20.03 (C-2, 18.82 ppm (CH3, ESI-MS (pos, 206.16, M+H, calcd. 206.15, HR ESI-MS pos, 206.1539, M+H, calcd. 206.1545
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+, calcd. 206.1545).
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32
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1642374541
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B. Kranke, D. Hebrault, M. Schultz-Kukula, H. Kunz, Synlett 2004, 671-674.
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(2004)
Synlett
, pp. 671-674
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Kranke, B.1
Hebrault, D.2
Schultz-Kukula, M.3
Kunz, H.4
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