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2
5
15. Compound 3a: mp 215°C. [h] =−160 (c 1, CHCl ). IR
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3
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500–1502; (c) Ooi, T.; Takeuchi, M.; Kameda, M.;
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6
0.90 (1H, m), 1.41 (1H, m), 1.80 (1H, m), 2.23 (1H, m),
2.56 (1H, app t, J=11.5), 2.94 (1H, br t, J=10.5) 3.78
(1H, br d, J=12.8,), 3.78 (1H, br d, J=12.8,), 4.08 (1H,
m,), 4.89 (1H, m), 5.08 (4H, dd, J=17.7, 12.2), 5.31 (2H,
d, J=4.3), 5.37 (d, J=11.6, 1H), 5.89 (1H, d, J=11.6),
6.42 (1H, br s), 6.49 (1H, s), 6.68 (1H, d, J=5.5), 6.88
(2H, s), 7.05 (2H, m), 7.28 (6H, m), 7.49 (4H, d, J=7.3),
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(1H, d, J=4.6). C NMR (75 MHz, CHCl ) l 22.7, 25.3,
3
7
041–7048.
26.4, 37.9, 50.2, 60.0, 62.2, 65.5, 66.7, 70.0, 104.7, 112.9,
118.0, 119.9, 123.2, 123.7, 127.7, 127.95, 128.0, 128.7,
128.9, 129.1, 136.2, 137.0, 149.0, 159.3.
7
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2
5
17. Compound 3b: mp 164°C. [h] =−136 (c 1, CHCl ). IR
D
3
(KBr) w 3409, 3040, 2939, 2878, 1596, 1454, 1381, 1347,
−
1 1
1300, 1159, 1072, 937, 857, 743, 696 cm . H NMR (300
1
948–1951; (c) Casas, J.; N a´ jera, C.; Sansano, J. M.;
MHz, CDCl ) l 1.36 (1H, m), 1.65 (1H, m), 2.00–2.23
3
Gonz a´ lez, J.; Sa a´ , J. M.; Vega, M. Tetrahedron: Asymme-
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(5H, m), 2.41 (1H, m), 2.90 (1H, t, J=11.7), 3.25 (1H,
m), 3.98 (1H, dd, J=12.5, 6.7), 4.15 (2H, m), 4.22 (1H,