PMR spectrum (CDCl , ꢈ, ppm, J/Hz): 0.77 (3H, s, H-15); 1.13–1.26 (2H, m, H-2); 1.36–1.73 (7H, m, H-1, H-3,
3
H-6, H-9a); 1.91–2.04 (1H, m, H-5); 2.13 (1H, dd, J = 1.88, J = 15.20, H-9b); 2.26–2.43 (2H, m, CH Ind); 2.73–3.11 (6H,
1
2
2
m, NCH , H-7, H-11, H-13); 3.85 (3H, s, OMe); 4.40 (1H, d, J = 1.17, H-14a); 4.73 (1H, d, J = 1.56, H-14b); 4.43 (1H, m,
2
H-8); 6.84 (1H, dd, J = 2.56, J = 8.54, H-6ꢀ); 7.01 (1H, d, J = 2.56, H-4ꢀ); 7.02 (1H, s, H-2ꢀ); 7.22 (1H, dd, J = 3.32,
1
2
1
J = 8.54, H-7ꢀ); 8.00 (1H, br.s, NH).
2
(3aR, 8aR, 9aR)-8a-Methyl-5-methylidene-3-(3, 4, 5, 6-tetrahydro-2H-[2, 3ꢀ]bipyridin-1-
+
ylmethyl)decahydronaphtho[2,3-b]furan-2-one (23). Found: m/z 394.2715 [M] , C H N O ; calcd: M = 394.2620.
UV spectrum (EtOH, ꢆ , nm, log ): 204 (4.59), 2.86 (3.63). IR spectrum (KBr, ꢇ, cm ): 962m, 1137m, 1263m, 1440m,
25 34
–1
2 2
max
1511m, 1758s (C=O), 2928m.
PMR spectrum (CDCl , ꢈ, ppm, J/Hz): 0.69 (3H, s, H-15); 0.79–0.97 (2H, m, H-2); 1.15–1.89 (13H, m, aliphatic
3
protons); 2.08 (1H, dd, J = 2.08, J = 15.35, H-9b); 2.22–2.48 (3H, m, H-5, H-7, H-6ꢀa); 2.90 (1H, dd, J = 3.02, J = 13.49,
1
2
1
2
H-6ꢀb); 3.05 (1H, m, H-2ꢀ); 3.17 (1H, dd, J = 3.02, J = 10.24, H-13b); 4.30 (1H, d, J = 1.39, H-14a); 4.71 (1H, d, J = 1.62,
1
2
H-14b); 4.31 (1H, m, H-8); 7.20-7.27 (1H, m, H-5ꢀꢀ); 7.70 (1H, dt, J = 1.86, J = 2.33, J = 7.91, H-4ꢀꢀ); 8.47 (1H, dd,
1
2
3
J = 1.86, J = 4.88, H-6ꢀꢀ); 8.52 (1H, dd, J = 0.69, J = 2.09, H-2ꢀꢀ).
1
2
1
2
(3aR,8aR,9aR)-3-((R)-6-Hydroxy-7-methoxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-8a-methyl-5-
+
methylidenedecahydronaphtho[2,3-b]furan-2-one (24). Found: m/z 425.2511 [M] , C H NO ; calcd: M = 425.2566.
26 35
4
–1
UV spectrum (EtOH, ꢆ , nm, log ): 202 (4.46), 234 (4.05), 310 (3.60). IR spectrum (KBr, ꢇ, cm ): 883m, 1082m, 1154m,
max
1761s (C=O), 2807m, 2926m, 2938m, 3502br.s (OH).
PMR spectrum (CDCl , ꢈ, ppm, J/Hz): 0.79 (3H, s, H-15); 1.12–1.45 (3H, m, H-2, H-9a); 1.30 (3H, d, J = 6.97,
3
Me-1ꢀ); 1.48–1.80 (6H, m, H-1, H-3, H-6); 1.90–2.04 (1H, m, H-7); 2.11–2.37 (2H, m, H-9b, H-5); 2.50–2.65 (2H, m, H-4ꢀ),
2.76 (1H, dd, J = 1.86, J = 5.82, H-13a); 2.85 (1H, dd, J = 1.86, J = 6.84, H-13b); 2.94–3.10 (3H, m, H-3ꢀ, H-11); 3.75 (1H,
1
2
1
2
q, J = 6.28, H-1ꢀ); 3.83 (3H, s, OMe); 4.44 (1H, d, J = 0.72, H-14a); 4.75 (1H, d, J = 0.72, H-14b); 4.48 (1H, m, H-8); 6.52 (1H,
d, J = 5.1, H-8ꢀ); 6.63 (1H, s, H-5ꢀ).
(3aR,8aR,9aR)-3-((R)-6,7-Dimethoxy-1-methyl-3,4-dihydro-1H-isoquinolin-2-ylmethyl)-8a-methyl-5-
+
methylidenedecahydronaphtho[2,3-b]furan-2-one (25). Found: m/z 439.2250 [M] , C H NO ; calcd: M = 439.2723.
27 37
–1
4
UV spectrum (EtOH, ꢆ , nm, log ): 205 (4.60), 284 (3.50). IR spectrum (KBr, ꢇ, cm ): 854m, 1116m, 1172s, 1222m,
max
1513m, 1762s (C=O), 2905m, 2931m, 2938m.
PMR spectrum (CDCl , ꢈ, ppm, J/Hz): 0.79 (3H, s, H-15); 1.13–1.41 (3H, m, H-2, H-9a); 1.35 (3H, d, J = 6.46,
3
Me-1ꢀ), 1.48–1.61 (4H, m, H-1, H-3); 1.74–1.83 (2H, m, H-6); 1.97 (1H, m, H-7); 2.16 (1H, dd, J = 1.95, J = 15.65, H-9b);
1
2
2.31 (1H, dt, J = 12.91, H-5); 2.48–2.71 (2H, m, H-4ꢀ), 2.75–2.91 (2H, m, H-13); 2.95–3.18 (3H, m, H-3ꢀ, H-11), 3.70 (1H,
q, J = 6.50, H-1ꢀ); 3.82 (6H, s, OMe); 4.43 (1H, d, J = 1.36, H-14a); 4.74 (1H, d, J = 1.36, H-14b); 4.48 (1H, m, H-8); 6.53 (2H,
s, H-5ꢀ, H-8ꢀ).
3-((3aR,8aR,9aR)-8a-Methyl-5-methylidene-2-oxodecahydronaphtho[2,3-b]furan-3-ylmethyl)-1,2,3,4,5,6-
+
hexahydro-1,5-methanopyrido[1,2-a][1,5]diazocin-8-one (26). Found: m/z 422.2272 [M] , C H N O ; calcd:
26 34
2
3
–1
M = 422.2569. UV spectrum (EtOH, ꢆ , nm, log ): 202 (4.34), 235 (3.95), 310 (4.02). IR spectrum (KBr, ꢇ, cm ): 960m,
max
1164m, 1552m, 1583m, 1651s and 1757s (C=O), 2906m, 2917m, 2937m.
PMR spectrum (CDCl , ꢈ, ppm, J/Hz): 0.71 (3H, s, H-15); 0.96–2.96 (23H, aliphatic protons); 3.77 (1H, dd,
3
J = 5.95, J = 15.65, H-6ꢀa); 3.94 (1H, d, J = 15.65, H-6ꢀb); 4.30 (1H, m, H-8); 4.35 (1H, d, J = 1.10, H-14a); 4.75 (1H, d,
1
2
J = 1.10, H-14b); 5.92 (1H, dd, J = 1.32, J = 9.04, H-11ꢀ); 6.36 (1H, dd, J = 1.32, J = 6.84, H-9ꢀ); 7.22 (1H, dd, J = 6.84,
1
2
1
2
1
J = 9.05, H-10ꢀ).
2
(3aR,5S,8aR,9aR)-3-{[((1R,2R)-2-Hydroxy-1-methyl-2-phenylethyl)methylamino]methyl}-5,8a-dimethyl-
+
3a,5,6,7,8,8a,9,9a-octahydro-3H-naphtho[2,3-b]furan-2-one (27). Found: m/z 397.2532 [M] , C H NO ; calcd:
25 35
3
–1
M = 397.2617. UV spectrum (EtOH, ꢆ , nm, log ): 204 (4.56). IR spectrum (KBr, ꢇ, cm ): 984m, 1038m, 1164m, 1760s
max
(C=O), 2933m, 3508 and 3527br.s (OH).
PMR spectrum (CDCl , ꢈ, ppm, J/Hz): 0.78 (3H, d, J = 6.75, NCHMe); 1.18 (3H, d, J = 7.67, H-14); 1.27 (3H, s,
3
H-15); 1.39–1.92 (7H, m, H-1, H-2, H-3, H-9a); 2.10 (1H, dd, J = 3.27, J = 14.89, H-9b); 2.37 (3H, s, NMe), 2.47–2.56 (1H,
1
2
m, H-4); 2.60–2.74 (2H, m, NCHMe, H-11); 2.89–3.10 (2H, m, H-13); 3.28 (1H, m, H-7); 4.29 (1H, d, J = 9.77, CHOH); 4.81
(1H, m, H-8); 5.35 (1H, d, J = 2.79, H-6); 7.32 (5H, s, H ).
arom
(3aR,5S,8aR,9aR)-3-{[2-(1H-Indol-3-yl)ethylamino]methyl}-5,8a-dimethyl-3a,5,6,7,8,8a,9,9a-octahydro-3H-
+
naphtho[2,3-b]furan-2-one (28). C H N O . Mass spectrum (EI, 70 eV, m/z, I , %): 392 (0.4) [M] , 217 (20), 176 (46),
25 32
2
2
rel
171 (81), 160 (71), 145 (61), 130 (100), 115 (77), 105 (81), 95 (80), 80 (76). UV spectrum (EtOH, ꢆ , nm, log ): 201
max
721