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6.81 (dd, 1H, J = 6.7, 9.0 Hz), 5.84 (dd, 1H, J = 1.5,
14.3 Hz), 4.16 (q, 2H, J = 7.5 Hz), 2.81–2.72 (m, 2H),
2.52–2.50 (m, 1H), 2.23–2.14 (m, 1H), 1.32–1.22 (m, 6H).
13C NMR (75 MHz, CDCl3): d 166.2, 148.0, 121.8, 60.3,
54.8, 45.9, 38.8, 15.7, 14.1; IR: 2924, 1720, 1268, 1183,
1036 cmꢁ1; MS (ESI) m/z 193 (M+Na)+. Compound 13:
[a]25 ꢁ4.02 (c 1.6, CHCl3); 1H NMR (300 MHz, CDCl3): d
7.38–7.21 (m, 5H), 6.85 (dd, 1H, J = 8.5, 15.6 Hz), 5.83
(dd, 1H, J = 1.5, 15.6 Hz), 4.73 (d, 1H, J = 11.7 Hz), 4.45
(d, 1H, J = 12.5 Hz) 4.16 (q, 2H, J = 7.0 Hz), 3.98 (tt, 1H,
J = 1.5, 6.2 Hz), 3.63 (q, 1H, J = 6.2 Hz), 2.58–2.30 (m,
3H), 2.23 (br s, 1H), 1.81–1.67 (m, 2H), 1.30 (t, 3H,
J = 7.0 Hz), 1.16 (d, 3H, J = 7.0 Hz), 1.00 (t, 3H,
J = 7.8 Hz); 13C NMR (75 MHz, CDCl3): d 166.5, 138.1,
133.6, 130.1, 128.4, 128.3, 127.8, 127.5, 82.3, 72.3, 70.4,
70.2, 60.3, 41.2 29.0, 25.4, 14.3, 14.2, 9.7; MS (ESI) m/z
345 (M+H)+; IR: 3424, 3030, 2925, 1718, 1276,
12. Evans, D. A.; Gauchet-Prunet, J. A. J. Org. Chem. 1993,
58, 2446–2453.
25
1019 cmꢁ1. Compound 1: Liquid ½aꢀD ꢁ33.8 (c 0.24,
13. Physical and analytical data matched with the reported
data. (a) See Ref. 1. (b) Chakraborty, T. K.; Rajib, K. G.:
Tetrahedron Lett. 2004, 45, 7637. Spectral data for
CHCl3); IR 3445, 2924, 1728, 1459, 1104 cmꢁ1 1H
,
NMR (400 MHz, CDCl3): d 4.71 (ddd, 1H, J = 2.5, 4.7,
8.1 Hz), 4.06 (ddd, 1H, J = 3.2, 3.4, 5.6 Hz), 3.55 (m, 1H),
2.81 (dd, 1H, J = 5.5, 18.5 Hz), 2.53 (ddd, 1H, J = 0.9,
3.2, 18.1 Hz), 1.95 (m, 1H), 1.74 (m, 1H), 1.65 (m, 2H),
1.50 (m, 3H), 1.42 (m, 2H), 0.95 (d, 3H, J = 7.2 Hz), 0.94
(t, 3H, J = 7.3 Hz); 13C NMR (75 MHz, CDCl3): d 170.3,
78.0, 73.0, 68.6, 37.3, 36.4, 35.8, 31.7, 30.3, 21.6, 10.2, 9.8;
MS (ESI) m/z 231 (M+H)+, 253 (M+Na)+.
25
compound 3: ½aꢀD ꢁ98.4 (c 2.2, CHCl3); 1H NMR
(300 MHz, CDCl3): d 7.32–7.23 (m, 5H), 4.75 (d, 1H,
J = 11.3 Hz), 4.44 (d, 1H, J = 11.3 Hz), 3.96 (t, 1H,
J = 6.0 Hz), 2.38 (s, 1H) 1.76 (m, 2H), 1.02 (t, 3H,
J = 6.7 Hz); MS (ESI) m/z 197 (M+Na)+. Compound 4:
25
½aꢀD ꢁ13.2 (c 1.1, CHCl3); 1H NMR (300 MHz, CDCl3): d