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2.0, 4J ¼ 1.6 Hz, 1H), 4.94–4.86 (m, 1H), 4.53 (dt, J ¼ 4.8, 1.6 Hz, 105.1, 90.0, 68.8, 46.6, 37.4, 27.2, 23.8. MS (EI) LRMS: m/z 298,
2H), 3.38 (*3.35, dt, J ¼ 6.4, 1.3 Hz, 2H), 2.52 (*2.68, s, 2H), 2.08– 269, 217 (100%), 175, 149, 91, 69.
2.01 (*1.89–1.84 (m), m, 2H), 1.73–1.47 (m, 2H), 1.36–1.10 (m,
3j 1H NMR (400 MHz, CDCl3) d 7.73 (d, 3J ¼ 8.7 Hz, 1H), 6.52
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9H), 0.82 (td, 3H). 13C NMR (100 MHz, CDCl3) d 192.0, 162.4, (d, J ¼ 8.7 Hz, 1H), 6.03 (ddt, J ¼ 17.7, 10.3, 4.8 Hz, 1H), 5.93
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158.1, 136.0, 132.7, 126.0, 117.4, 116.3, 114.9, 104.9, 79.5, 68.9, (ddt, J ¼ 14.2, 12.8, 6.4 Hz, 1H), 5.41 (dq, J ¼ 17.2, 2.0, J ¼
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48.7, 39.2, 36.3, 34.6, 28.2, 27.8, 27.5, 27.3, 19.9, 14.3. MS (EI) 1.6 Hz, 1H), 5.28 (dq, J ¼ 10.6, 2.0, J ¼ 1.2 Hz, 1H), 5.05 (dq,
LRMS: m/z 354, 269, 217 (100%), 175, 149, 91, 41 (90%).
3J ¼ 17.0, 2.0, 4J ¼ 1.6 Hz, 1H), 4.96 (dq, 3J ¼ 9.9, 2.0, 4J ¼ 1.3 Hz,
3e 1H NMR (400 MHz, CDCl3) d 7.68 (d, 3J ¼ 8.7 Hz, 1H), 6.46 1H), 4.59 (dt, J ¼ 4.8, 1.6 Hz, 2H), 3.44 (dt, J ¼ 6.4, 1.3 Hz, 2H),
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(d, J ¼ 8.7 Hz, 1H), 5.97 (ddt, J ¼ 17.7, 10.3, 4.8 Hz, 1H), 5.87 2.66 (s, 2H), 2.13–2.03 (m, 2H), 1.77–1.63 (m, 4H), 1.59–1.51 (m,
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(ddt, J ¼ 14.2, 12.8, 6.4 Hz, 1H), 5.35 (dq, J ¼ 17.2, 2.0, J ¼ 4H), 1.47–1.38 (m, 2H)$13C NMR (100 MHz, CDCl3) d 191.9,
1.6 Hz, 1H), 5.21 (dq, 3J ¼ 10.6, 2.0, 4J ¼ 1.2 Hz, 1H), 5.00 (dq, 3J 162.3, 158.5, 136.0, 132.7, 125.9, 117.3, 116.4, 115.1, 114.7,
¼ 17.0, 2.0, 4J ¼ 1.6 Hz, 1H), 4.94–4.86 (m, 1H), 4.54 (dt, J ¼ 4.8, 104.9, 84.2, 68.9, 48.7, 38.4, 29.3, 27.4, 22.0. MS (EI) LRMS: m/z
1.6 Hz, 2H), 3.39 (*3.35, dt, J ¼ 6.4, 1.3 Hz, 2H), 2.53 (*2.68, s, 326, 269, 217 (100%), 175, 149, 91, 55.
2H), 2.08–2.01 (*1.89–1.84, m, 2H), 1.73–1.56 (m, 2H), 1.37–1.10
5a1H NMR (400 MHz, CDCl3) d 7.69 (d, 3J ¼ 8.7 Hz, 1H), 6.48
(m, 13H), 0.81 (td, 3H). 13C NMR (100 MHz, CDCl3) d 192.0, (d, J ¼ 8.7 Hz, 1H), 5.99 (ddt, J ¼ 14.3, 10.3, 5.0 Hz, 1H), 5.90
162.4, 158.1, 136.0, 132.7, 126.0, 117.4, 114.9, 104.9, 79.6, 68.9, (ddt, J ¼ 21.0, 9.3, 3.0 Hz, 1H), 5.37 (dq, 3J ¼ 17.0, 2.0, 4J ¼
48.7, 36.9, 36.6, 34.6, 32.1, 27.8, 27.5, 26.5, 22.6, 14.0. MS (EI) 1.7 Hz, 1H), 5.20 (dq, 3J ¼ 10.7, 2.0, 4J ¼ 1.2 Hz, 1H), 5.02 (dq, 3J
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LRMS: m/z 382, 341, 269, 217 (100%), 175, 149, 43, 41 (100%).
¼ 17.0, 2.0, 4J ¼ 1.5 Hz, 1H), 4.93 (dq, 3J ¼ 10.0, 2.0, 4J ¼ 1.2 Hz,
3f 1H NMR (400 MHz, CDCl3) d 7.78 (d, 3J ¼ 8.7 Hz, 1H), 7.34– 1H), 4.52 (dt, J ¼ 5.0, 1.5 Hz, 2H), 3.39 (dt, J ¼ 6.2, 1.5 Hz, 2H),
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7.21 (m, 5H), 6.56 (d, J ¼ 8.7 Hz, 1H), 6.09–5.96 (m, 2H), 5.43 2.57 (s, 2H), 2.50 (td, 2H), 2.36 (td, 2H), 2.24 (s, 3H), 1.99 (brd,
(dq, 3J ¼ 17.2, 2.0, 4J ¼ 1.6 Hz, 1H), 5.30 (dq, 3J ¼ 10.6, 2.0, 4J ¼ 2H), 1.78–1.71 (m, 2H). 13C NMR (100 MHz, CDCl3) d 190.2,
1.2 Hz, 1H), 5.09 (dq, 3J ¼ 17.0, 2.0, 4J ¼ 1.6 Hz, 1H), 5.01 (dq, 3J 161.5, 156.8, 134.8, 131.6, 125.1, 116.4, 115.3, 114.0, 104.2, 67.9,
¼ 9.9, 2.0, 4J ¼ 1.3 Hz, 1H), (m, 1H), 4.62 (dt, J ¼ 5.0, 1.5 Hz, 2H), 49.8, 45.0, 33.4, 26.4. MS (EI) LRMS: m/z 327, 326, 175, 110, 109,
3.55 (dt, J ¼ 6.2, 1.5 Hz, 2H), 2.67 (*2.91, s, 2H), 2.57 (tt, 1H), 96, 70 (100%).
2.31–2.13 (m, 2H), 1.97 (qd, 2H), 1.78–1.72 (m, 2H), 1.52 (dd,
5b 1H NMR (400 MHz, CDCl3) d 7.69 (d, 3J ¼ 8.7 Hz, 1H), 6.48
2H). 13C NMR (100 MHz, CDCl3) d 191.7, 162.5, 158.0, 146.6, (d, J ¼ 8.7 Hz, 1H), 6.03 (ddt, J ¼ 14.3, 10.3, 5.0 Hz, 1H), 5.94
136.0, 132.7, 128.4, 126.8, 126.1, 117.4, 116.3, 115.0, 105.1, 78.8, (ddt, J ¼ 21.0, 9.3, 3.0 Hz, 1H), 5.42 (dq, 3J ¼ 17.0, 2.0, 4J ¼
69.0, 48.7, 43.3, 34.9, 28.8, 27.4. MS (EI) LRMS: m/z 388, 360 1.7 Hz, 1H), 5.29 (dq, 3J ¼ 10.7, 2.0, 4J ¼ 1.2 Hz, 1H), 5.06 (dq, 3J
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(98%), 241 (100%), 189, 91, 77.
¼ 17.0, 2.0, 4J ¼ 1.5 Hz, 1H), 4.99 (dq, 3J ¼ 10.0, 2.0, 4J ¼ 1.2 Hz,
3g 1H NMR (400 MHz, CDCl3) d 7.73 (d, 3J ¼ 8.5 Hz, 1H), 6.68 1H), 4.60 (dt, J ¼ 5.0, 1.5 Hz, 2H), 3.47 (dt, J ¼ 6.2, 1.5 Hz, 2H),
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(d, J ¼ 8.5, 1H), 5.91 (pt, J ¼ 5.7 2.0 Hz, 1H), 5.58 (dhpt, J ¼ 2.58 (s, 2H) 2.39 (td, 3H), 2.25 (*t, d, 2H), 1.96 (brd, 2H), 1.78–
11.2, 1.7 Hz, 1H), 4.64–4.61 (m, 2H), 4.01–3.93 (m, 4H), 3.59– 1.71 (m, 4H), 1.42 (sxt, 2H), 0.85 (t, 3H). 13C NMR (100 MHz,
3.57 (m, 2H), 2.67 (s, 2H), 2.14–2.09 (m, 2H), 1.91 (td, 2H), 1.78– CDCl3) d 190.3, 161.5, 156.8, 134.9, 131.6, 125.1, 116.4, 114.0,
1.71 (m, 2H), 1.64 (brd, 2H). 13C NMR (125 MHz, CDCl3) d 209.7, 104.2, 76.8, 67.9, 59.6, 47.8, 33.4, 26.4, 19.1, 10.9. MS (EI) LRMS:
180.8, 176.2, 154.1, 150.9, 144.4, 135.8, 133.3, 126.3, 123.5, 97.1, m/z 355, 326 (100%), 110, 98, 70.
87.3, 82.7, 82.5, 65.9, 50.7, 48.5, 45.8. MS (EI) LRMS: m/z 330,
5c 1H NMR (400 MHz, CDCl3) d 7.76 (d, 3J ¼ 8.7 Hz, 1H), 6.55
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231, 177, 99 (100%), 86.
(d, J ¼ 8.7 Hz, 1H), 6.03 (ddt, J ¼ 12.8, 10.3, 5.0 Hz, 1H), 5.94
3h 1H NMR (400 MHz, CDCl3) d 7.68 (d, 3J ¼ 8.7 Hz, 1H), 6.47 (ddt, J ¼ 16.3, 10.0, 3.7 Hz, 1H), 5.42 (dq, J ¼ 17.0, 2.0, J ¼
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(d, J ¼ 8.7 Hz, 1H), 5.95 (ddt, J ¼ 17.2, 10.3, 4.8 Hz, 1H), 5.85 1.7 Hz, 1H), 5.29 (dq, 3J ¼ 10.7, 2.0, 4J ¼ 1.5 Hz, 1H), 5.06 (dq, 3J
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(ddt, J ¼ 14.2, 12.8, 6.4 Hz, 1H), 5.34 (dq, J ¼ 17.2, 2.0, J ¼ ¼ 17.0, 2, 4J ¼ 1.5 Hz, 1H), 4.99 (dq, 3J ¼ 10.0, 2.0, 4J ¼ 1.2 Hz,
1.6 Hz, 1H), 5.21 (dq, 3J ¼ 10.3, 2.0, 4J ¼ 1.2 Hz, 1H), 4.97 (dq, 3J 1H), 4.60 (dt, J ¼ 5.0, 1.5 Hz, 2H), 3.47 (dt, J ¼ 6.2, 1.5 Hz, 2H),
¼ 17.0, 2.0, 4J ¼ 1.6 Hz, 1H), 4.90 (dq, 3J ¼ 9.9, 2.0, 4J ¼ 1.3 Hz, 2.77 (hpt, 1H), 2.65 (s, 2H) 2.64–2.56 (m, 4H), 2.06 (brd, 2H),
1H), 4.53 (dt, J ¼ 4.8, 1.6 Hz, 2H), 3.46 (s, 2H), 3.38 (s, 4H), 2.56 1.77–1.70 (m, 2H), 1.07 (d, 6H).$13C NMR (100 MHz, CDCl3)
(s, 2H), 1.96 (t, 4H), 1.78–1.71 (m, 2H), 1.56 (td, 2H), 0.89 (s, 6H). d 191.3, 162.5, 157.8, 135.9, 132.6, 126.1, 120.4, 118.3, 117.5,
13C NMR (100 MHz, CDCl3) d 190.4, 161.5, 156.9, 134.8, 131.6, 116.3, 114.9, 105.2, 3.9, 78.0, 69.0, 54.6, 47.7, 44.0, 34.6, 33.3,
125.1, 116.4, 115.4, 113.9, 104.2, 95.8, 78.2, 69.1, 69.0, 67.9, 46.6, 27.9, 27.4, 24.8, 21.5, 18.3. MS (EI) LRMS: m/z 355, 340 (100%),
30.0, 29.1, 26.4, 21.6. MS (EI) LRMS: m/z 412, 217, 141 (100%), 284, 124, 56, 41.
128, 69.
5d 1H NMR (400 MHz, CDCl3) d 7.75 (d, 3J ¼ 8.7 Hz, 1H), 7.31
3i 1H NMR (400 MHz, CDCl3) d 7.76 (d, 3J ¼ 8.7 Hz, 1H), 6.54 (s, 5H), 6.54 (d, 3J ¼ 8.7 Hz, 1H), 6.04 (ddt, J ¼ 17.1, 10.5, 5.0 Hz,
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(d, J ¼ 8.7 Hz, 1H), 6.03 (ddt, J ¼ 17.7, 10.3, 4.8 Hz, 1H), 5.90 1H), 5.94 (ddt, J ¼ 14.7, 12.7, 6.2 Hz, 1H), 5.40 (dq, 3J ¼ 17.3, 2.0,
(ddt, J ¼ 14.2, 12.8, 6.4 Hz, 1H), 5.42 (dq, J ¼ 17.2, 2.0, J ¼ 4J ¼ 1.5 Hz, 1H), 5.28 (dq, J ¼ 10.0, 2.0, J ¼ 1.2 Hz, 1H), 5.08
1.6 Hz, 1H), 5.29 (dq, 3J ¼ 10.6, 2.0, 4J ¼ 1.2 Hz, 1H), 5.01 (dq, 3J (dq, 3J ¼ 17.3, 2.0, 4J ¼ 1.5 Hz, 1H), 5.01 (dq, 3J ¼ 10.0, 2.0, 4J ¼
¼ 17.0, 2.0, 4J ¼ 1.6 Hz, 1H), 4.94 (dq, 3J ¼ 9.9, 2.0, 4J ¼ 1.3 Hz, 1.2 Hz, 1H), 4.60 (dt, J ¼ 4.7, 1.7 Hz, 2H), 3.55 (s, 2H), 3.44 (d,
1H), 4.60 (dt, J ¼ 4.8, 1.6 Hz, 2H), 3.39 (dt, J ¼ 6.4, 1.3 Hz, 2H), 2H), 2.64 (s, 2H) 2.63–2.60 (m, 2H), 2.46 (t, 2H), 2.04 (d, 2H),
2.77 (s, 2H), 2.09–2.03 (m, 2H), 1.91–1.83 (m, 2H), 1.76–1.67 (m, 1.76–1.70 (m, 2H). 13C NMR (100 MHz, CDCl3) d 191.3, 162.5,
2H), 1.65–1.58 (m, 2H). 13C NMR (100 MHz, CDCl3) d 191.7, 157.9, 132.6, 129.2, 127.1, 128.2, 127.1, 126.1, 138.0, 117.5,
162.1, 159.0, 136.0, 132.7, 126.1, 117.3, 116.5, 115.3, 114.5,
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This journal is © The Royal Society of Chemistry 2018
RSC Adv., 2018, 8, 38673–38680 | 38677