P. Durand et al. / Tetrahedron Letters 42 (2001) 2121–2124
2123
tible to demonstrate TGF-b activity. These results will
28.19, 28.84, 30.75, 31.88, 53.36, 77.86, 124.38, 131.25,
155.58, 174.28. IR 1712, 1503, 1397, 1366 cm−1. ESI+-MS
(MH+): 286. Anal. calcd for C15H27NO4: C, 63.13; H,
9.54; N, 4.91. Found: C, 62.84; H, 9.74; N, 5.22.
27. Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett.
1990, 31, 205–208.
be published in the near future.
References
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8-enoyl}amino)-2-methylpropanoyl]-L-phenylalanyl-D-proli-
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nate (10): mp 42°C; Rf 0.3 [cyclohexane–EtOAc (40:60)];
[h]2D2=+35.5° (c 0.18, MeOH); lH (300 MHz, CDCl3):
1.20–1.70 (26H, m), 1.75–2.10 (6H, m), 2.70–3.20 (3H,
m), 3.50–3.65 (1H, m), 3.69 (3H, s), 3.85–4.05 (1H, m),
4.25–4.35 (1H, m), 4.85–4.95 (1H, m), 5.00–5.10 (1H, bs),
5.35–5.45 (2H, m), 6.73 (1H, s), 6.85 (1H, d, J=8.2 Hz),
7.15–7.35 (5H, m); lC (75.47 MHz, CDCl3): 17.87, 24.40,
24.58, 25.28, 25.42, 28.30 (3), 28.78, 28.94, 29.34, 32.17,
32.39, 39.22, 46.72, 52.15, 52.57, 55.07, 56.98, 58.77,
80.10, 124.76, 126.92, 128.36 (2), 129.54 (2), 131.33,
136.37, 155.79, 169.61, 171.56, 172.16, 173.56; IR 1740,
1670, 1635, 1503, 1451 cm−1; ESI+-MS (MH+): 629. Anal.
calcd for C34H52N4O7: C, 64.94; H, 8.34; N, 8.91. Found:
C, 64.31; H, 8.48; N, 8.78.
29. (3S,9S,14aR)-9-Benzyl-3-[(6R,7R)-6,7-dihydroxyoctyl]-6,
6-dimethyldecahydropyrrolo[1,2- a][1,4,7,10]tetraazacyclo-
dodecine-1,4,7,10-tetrone (1): mp 82°C (lit.7 74–76°C); Rf
0.12 [EtOAc]; [h]D25=−55.6° (c 0.19, MeOH) [lit.7 [h]2D5=
−30.3° (c 0.19, MeOH)]; lH (300 MHz, CDCl3): 1.20 (3H,
d, J=6.3 Hz), 1.25–1.95 (19H, m), 2.10–2.45 (4H, 2
exchangeable, m), 2.94 (1H, dd, J=5.5 Hz, 13.5 Hz),
3.15–3.40 (3H, m), 3.55–3.65 (1H, m), 3.80–3.90 (1H, m),
4.15–4.25 (1H, m), 4.65 (1H, dd, J=2.0, 8.0 Hz), 5.15
(2H, dt, J=5.5, 10.0 Hz), 6.09 (1H, s), 7.14 (1H, d, J=10
Hz), 7.20–7.35 (5H, m), 7.52 (1H, d, J=10 Hz); lC (75.4
MHz, CDCl3): 19.50, 23.57, 24.70, 24.99, 25.28 (2), 26.44,
28.85, 29.13, 33.01, 35.82, 46.95, 53.40, 54.39, 57.76,
58.76, 70.90, 76.13, 126.68, 128.57 (2), 129.00 (2), 136.97,
171.89, 172.83, 174.43, 175.56; IR (KBr): 3400, 3300,
1680, 1670, 1660, 1620, 1520 cm−1; ESI−-MS (M−H)−
529. Anal. calcd for C28H42N4O6·0.67H2O: C, 61.96; H,
8.05; N, 10.32. Found: C, 61.51; H, 7.86; N, 10.37.
30. (3S,9S,14aR)-9-Benzyl-6,6-dimethyl-3-[(6E)-oct-6-enyl]-
decahydropyrrolo[1,2 - a][1,4,7,10]tetraazacyclododecine - 1,
4,7,10-tetrone (11): Rf 0.5 [cyclohexane–EtOAc (50:50)];
mp 55°C; [h]2D6=−60.4° (c 0.19, MeOH); lH (250 MHz,
CDCl3): 1.1–1.4 (6H, m), 1.34 (3H, s), 1.77 (3H, s),
1.55–2.05 (12H, m), 2.10–2.40 (2H, m), 2.95 (1H, dd,
J=5.8, 13.5 Hz), 3.15–3.35 (2H, m), 3.8–3.9 (1H, m), 4.18
(1H, dt, J=7.5, 10.3 Hz), 4.65 (1H, dd, J=2.5, 8.0 Hz),
5.10–5.25 (1H, m), 5.35–5.45 (2H, m), 5.90 (1H, s), 7.07
(1H, d, J=10.2 Hz), 7.15–7.35 (5H, m), 7.53 (1H, d,
J=10.2 Hz); lC (62.9 MHz, CDCl3): 17.90, 23.54, 24.72,
25.01, 25.38, 26.51, 28.72, 28.89, 29.25, 32.36, 35.77,
46.96, 53.41, 54.39, 57.76, 58.77, 124.79, 126.67, 128.58
(2), 129.02 (2), 131.28, 137.04, 171.74, 172.74, 174.42,
175.65; IR 1662, 1626, 1523 cm−1; ESI−-MS (M−H)−: 495.
Anal. calcd for C28H40N4O4·0.55H2O: C, 66.39; H, 8.18;
N, 11.06. Found: C, 63.97; H, 8.29; N, 11.26.
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0.19, MeOH); lH (300 MHz, d6-DMSO): 1.10–1.45 (15H,
m), 1.50–1.70 (5H, m), 1.85–2.00 (2H, m), 3.75–3.90 (1H,
m), 5.30–5.50 (2H, m), 7.01 (1H, d, J=8.0 Hz), 12.0–13.0
(1H, bs); lC (75.47 MHz, d6-DMSO): 17.71, 25.37, 28.07,
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