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4.7.3. Methyl (S)-2-[(2E,4E)-hexadienoyl]-7-(2-{5-methyl-2-
[(1E)-3-methylbuten-1-yl]oxazol-4-yl}ethoxy)-1,2,3,4-
tetrahydroisoquinoline-3-carboxylate (13c)
J = 6.6 Hz), 4.39–5.20 (2H, m), 5.42–5.65 (1H, m), 6.00–6.87 (7H,
m), 7.04 (1H, d, J = 8.1 Hz), 7.18–7.51 (1H, m). IR (neat) cmꢁ1
:
3462, 2955, 2928, 2870, 1740, 1653, 1630, 1533, 1506.
Yield 54%. 1H NMR (CDCl3) d: 1.08 (6H, d, J = 6.6 Hz), 1.80–1.95
(3H, m), 2.20–2.80 (1H, m), 2.27 (3H, s), 2.87 (2H, t, J = 6.6 Hz),
3.00–3.30 (2H, m), 3.60 (3H, s), 4.15 (2H, t, J = 6.6 Hz), 4.50–5.15
(2H, m), 5.40–5.70 (1H, m), 6.00–6.90 (7H, m), 7.04 (1H, d,
J = 8.2 Hz), 7.15–7.55 (1H, m). IR (neat) cmꢁ1: 2957, 2928, 2872,
1739, 1651, 1614, 1533, 1506.
4.7.10. Methyl (S)-2-[(2E,4E)-hexadienoyl]-7-(2-{5-methyl-2-
[(1E)-3-methylhexen-1-yl]oxazol-4-yl}ethoxy)-1,2,3,4-
tetrahydroisoquinoline-3-carboxylate (13j)
Yield 81%. 1H NMR (CDCl3) d: 0.89 (3H, t, J = 7.1 Hz), 1.06 (3H, d,
J = 6.6 Hz), 1.29–1.40 (4H, m), 1.87 (3H, d, J = 6.6 Hz), 2.28 (3H, s),
2.29–2.35 (1H, m), 2.88 (2H, t, J = 6.6 Hz), 3.00–3.25 (2H, m), 3.60
(3H, s), 4.14 (2H, t, J = 6.6 Hz), 4.52, 4.94 (0.6H, AB-q, J = 17.2 Hz),
4.70, 4.77 (1.4H, AB-q, J = 15.4 Hz), 4.85–5.53 (1H, m), 6.07–6.75
(7H, m), 7.00–7.10 (1H, m), 7.34 (1H, dd, J = 14.9, 11.0 Hz). IR (neat)
cmꢁ1: 2957, 2928, 1740, 1655, 1628, 1612, 1506.
4.7.4. Methyl (S)-7-(2-{2-[(1E)-3,3-dimethylbuten-1-yl]-5-
methyloxazol-4-yl}ethoxy)-2-[(2E,4E)-hexadienoyl]-1,2,3,4-
tetrahydroisoquinoline-3-carboxylate (13d)
Yield 78%. 1H NMR (CDCl3) d: 1.11 (9H, s), 1.85 (3H, d,
J = 5.0 Hz), 2.28 (3H, s), 2.87 (2H, t, J = 6.8 Hz), 3.01–3.35 (2H, m),
3.60 (3H, s), 4.15 (2H, t, J = 6.8 Hz), 4.39–5.08 (2H, m), 5.38–5.65
(1H, m), 6.00–7.50 (9H, m). IR (neat) cmꢁ1: 3464, 3020, 2959,
2868, 1740, 1657, 1628, 1531.
4.7.11. Methyl (S)-7-(2-{2-[(1E)-1,5-dimethylhexen-1-yl]-5-
methyloxazol-4-yl}ethoxy)-2-[(2E,4E)-hexadienoyl]-1,2,3,4-
tetrahydroisoquinoline-3-carboxylate (13k)
Yield 78%. 1H NMR (CDCl3) d: 0.91 (6H, d, J = 6.6 Hz), 1.34 (2H,
dt, J = 7.8, 7.6 Hz), 1.55–1.64 (1H, m), 1.82–1.88 (3H, m), 2.02
(3H, s), 2.21 (2H, dt, J = 7.8, 7.3 Hz), 2.28 (3H, s), 2.89 (2H, t,
J = 6.8 Hz), 3.00–3.25 (2H, m), 3.60 (3H, s), 4.14 (2H, t, J = 6.6 Hz),
4.52, 4.93 (0.4H, AB-q, J = 17.3 Hz), 4.70, 4.77 (1.6H, AB-q,
J = 15.4 Hz), 4.85–5.20 (1H, m), 6.06–6.36 (3H, m), 6.43 (1H, t,
J = 7.6 Hz), 6.60–6.75 (1H, m), 6.72 (1H, m), 7.01 (1H, d,
J = 8.3 Hz), 7.33 (1H, dd, J = 14.7, 10.8 Hz). IR (neat) cmꢁ1: 1740,
1657, 1628, 1614, 1535, 1506.
4.7.5. Methyl (S)-2-[(2E,4E)-hexadienoyl]-7-(2-{5-methyl-2-
[(1E)-4-methylpenten-1-yl]oxazol-4-yl}ethoxy)-1,2,3,4-
tetrahydroisoquinoline-3-carboxylate (13e)
Yield 96%. 1H NMR (CDCl3) d: 0.94 (6H, d, J = 6.4 Hz), 1.50–1.95
(4H, m), 2.11 (2H, t, J = 7.0 Hz), 2.28 (3H, s), 2.87 (2H, t, J = 6.6 Hz),
3.00–3.30 (2H, m), 3.60 (3H, s), 4.15 (2H, t, J = 6.6 Hz), 4.50–5.15
(2H, m), 5.40–5.70 (1H, m), 6.00–6.90 (7H, m), 7.04 (1H, d,
J = 8.2 Hz), 7.15–7.55 (1H, m). IR (neat) cmꢁ1: 1740, 1655, 1628,
1533, 1508.
4.7.6. Methyl (S)-7-(2-{2-[(1E)-3,3-dimethylpenten-1-yl]-5-
methyloxazol-4-yl}ethoxy)-2-[(2E,4E)-hexadienoyl]-1,2,3,4-
tetrahydroisoquinoline-3-carboxylate (13f)
4.7.12. Methyl (S)-2-[(2E,4E)-hexadienoyl]-7-{2-[5-methyl-2-(5-
methylhexyl)oxazol-4-yl]ethoxy}-1,2,3,4-
tetrahydroisoquinoline-3-carboxylate (13l)
Yield 79%. 1H NMR (CDCl3) d: 0.83 (3H, t, J = 7.0 Hz), 1.06 (6H, s),
1.42 (2H, q, J = 7.0 Hz), 1.75–1.95 (3H, m), 2.28 (3H, s), 2.87 (2H, t,
J = 6.8 Hz), 3.01–3.24 (2H, m), 3.59 (3H, s), 4.15 (2H, t, J = 6.8 Hz),
4.33–5.02 (2H, m), 5.40–5.66 (1H, m), 6.06–6.80 (7H, m), 7.04
(1H, d, J = 8.1 Hz), 7.16–7.53 (1H, m). IR (neat) cmꢁ1: 3466, 2963,
2924, 2878, 1740, 1653, 1628, 1614, 1531, 1506.
Yield 88%. 1H NMR (CDCl3) d: 0.85 (6H, d, J = 6.8 Hz), 1.13–1.23
(2H, m), 1.29–1.39 (2H, m), 1.53 (1H, heptet, J = 6.8 Hz), 1.70 (2H,
quintet, J = 7.6 Hz), 1.79–1.91 (3H, m), 2.23 (3H, s), 2.65 (2H, t,
J = 7.6 Hz), 2.85 (2H, t, J = 7.6 Hz), 3.00–3.09 (1H, m), 3.14–3.26
(1H, m), 3.60 (3H, s), 4.53 (0.3H, d, J = 17.3 Hz), 4.70 (0.7H, d,
J = 15.6 Hz), 4.77 (0.7H, d, J = 15.6 Hz), 4.87–4.93 (0.3H, m), 4.94
(0.3H, d, J = 17.3 Hz), 5.48–5.56 (0.7H, m), 6.04–6.35 (3H, m),
6.55–6.76 (2H, m), 6.98–7.07 (1H, m), 7.27–7.39 (1H, m). IR (neat)
cmꢁ1: 1740, 1655, 1629, 1614, 1578, 1506.
4.7.7. Methyl (S)-7-(2-{2-[(1E)-4,4-dimethylpenten-1-yl]-5-
methyloxazol-4-yl}ethoxy)-2-[(2E,4E)-hexadienoyl]-1,2,3,4-
tetrahydroisoquinoline-3-carboxylate (13g)
Yield 79%. 1H NMR (CDCl3) d: 0.94 (9H, s), 1.75–1.95 (3H, m),
2.10 (2H, d, J = 7.7 Hz), 2.28 (3H, s), 2.87 (2H, t, J = 6.7 Hz), 3.00–
3.30 (2H, m), 3.61 (3H, s), 4.15 (2H, t, J = 6.7 Hz), 4.50–5.15 (2H,
m), 5.40–5.70 (1H, m), 6.00–6.90 (7H, m), 7.03 (1H, d, J = 8.3 Hz),
7.15–7.55 (1H, m).
4.7.13. Methyl (S)-2-hexanoyl-7-(2-{5-methyl-2-[(1E)-5-
methylhexen-1-yl]oxazol-4-yl}ethoxy)-1,2,3,4-
tetrahydroisoquinoline-3-carboxylate (15d)
Yield 89%. 1H NMR (CDCl3) d: 0.90 (6H, d, J = 6.6 Hz), 0.91 (3H, t,
J = 6.9 Hz), 1.30–1.43 (6H, m), 1.45–1.77 (3H, m), 2.18–2.27 (2H,
m), 2.28 (3H, s), 2.42–2.50 (2H, m), 2.88 (2H, t, J = 6.6 Hz), 3.00–
3.30 (2H, m), 3.60 (3H, s), 4.15 (2H, t, J = 6.6 Hz), 4.30–5.60 (3H,
m), 6.18 (1H, dt, J = 15.9, 1.4 Hz), 6.18 (1H, dt, J = 15.9, 7.1 Hz),
6.60–6.80 (2H, m), 6.99–7.05 (1H, m). IR (neat) cmꢁ1: 1743,
1657, 1614, 1587, 1533, 1506.
4.7.8. Methyl (S)-7-(2-{2-[(1E)-3-ethylpenten-1-yl]-5-
methyloxazol-4-yl}ethoxy)-2-[(2E,4E)-hexadienoyl]-1,2,3,4-
tetrahydroisoquinoline-3-carboxylate (13h)
Yield 79%. 1H NMR (CDCl3) d: 0.87 (6H, t, J = 7.5 Hz), 1.10–1.70
(4H, m), 1.70–2.20 (1H, m), 1.85 (3H, d, J = 4.8 Hz), 2.28 (3H, s),
2.87 (2H, t, J = 6.8 Hz), 3.00–3.30 (2H, m), 3.59 (3H, s), 4.15 (2H,
t, J = 6.8 Hz), 4.50–5.65 (3H, m), 5.80–6.50 (5H, m), 6.55–6.80
(2H, m), 7.03 (1H, d, J = 8.4 Hz), 7.15–7.50 (1H, m). IR (neat)
cmꢁ1: 1740, 1655, 1628, 1605, 1533, 1506.
4.7.14. Methyl (S)-2-(5-hexenoyl)-7-(2-{5-methyl-2-[(1E)-5-
methylhexen-1-yl]oxazol-4-yl}ethoxy)-1,2,3,4-
tetrahydroisoquinoline-3-carboxylate (15e)
Yield 93%. 1H NMR (CDCl3) d: 0.90 (6H, d, J = 6.6 Hz), 1.35 (2H,
dt, J = 7.8, 6.8 Hz), 1.54–1.68 (1H, m), 1.74–1.87 (2H, m), 2.09–
2.27 (4H, m), 2.28 (3H, s), 2.47 (2H, dd, J = 8.3, 6.6 Hz), 2.87 (2H,
t, J = 6.8 Hz), 3.00–3.30 (2H, m), 3.60 (3H, s), 4.14 (2H, t,
J = 6.8 Hz), 4.30–5.90 (6H, m), 6.19 (1H, dt, J = 15.9, 1.4 Hz), 6.59
(1H, dt, J = 15.9, 7.1 Hz), 6.60–7.05 (3H, m). IR (neat) cmꢁ1: 1744,
1651, 1614, 1589, 1533, 1506.
4.7.9. Methyl (S)-2-[(2E,4E)-hexadienoyl]-7-(2-{5-methyl-2-
[(1E)-5-methylhexen-1-yl]oxazol-4-yl}ethoxy)-1,2,3,4-
tetrahydroisoquinoline-3-carboxylate (13i)
Yield 67%. 1H NMR (CDCl3) d: 0.90 (6H, d, J = 6.2 Hz), 1.14–1.72
(3H, m), 1.86 (3H, d, J = 5.0 Hz), 2.05–2.40 (2H, m), 2.27 (3H, s), 2.87
(2H, t, J = 6.6 Hz), 3.00–3.25 (2H, m), 3.60 (3H, s), 4.15 (2H, t,