13C NMR (CDCl3, 125 MHz): d 203.3 (CH), 199.3 (C), 155.8 (C),
150.9 (CH), 131.7 (C), 129.9 (CH), 129.4 (two CH), 114.5 (two
CH), 56.5 (CH), 55.2 (CH3), 47.1 (CH), 46.8 (CH), 44.9 (CH2),
41.0 (CH), 31.3 (CH2), 25.9 (CH2); MS (m/z, relative intensity):
284 (M+, 20), 213 (3), 164 (9), 147 (6), 128 (4), 121 (100), 108 (13),
91 (8), 77 (7), 65 (4); exact mass calculated for C18H20O3 (M+):
284.1412; found 284.1414.
299 (M+, 26), 264 (45), 236 (71),180 (36), 146 (46), 130 (60), 120
(100), 115 (72), 91 (67), 77 (78), 55 (88); exact mass calculated for
C17H17NO4 (M+): 299.1158; found 299.1162.
(1R,2R,4aS,8aR)-1,2,3,4,4a,5,6,8a-Octahydro-1-(naphthalen-
1-yl)-6-oxonaphthalene-2-carbaldehyde (5g). Rf = 0.43 for 5g
in 40% EtOAc–hexane, pale yellow oil, 71% yield. Selected
spectroscopic data for 5g: [a]2D5 +18.2 (c 3.5 CHCl3); IR (neat):
2926, 2863, 1717, 1683, 1507, 1457, 1260, 1102, 818, 774, 750 cm-1;
1H NMR (CDCl3, 500 MHz): d 1.49–1.66 (m, 2 H), 1.91–2.04 (m,
2 H), 2.04–2.14 (m, 1 H), 2.20–2.31 (m, 1 H), 2.47–2.59 (m, 2 H),
2.78–2.86 (m, 1 H), 2.86–2.95 (m, 1 H), 5.85 (d, J = 9.77 Hz,
1 H), 6.46 (d, J = 10.01 Hz, 1 H), 7.37 (d, J = 8.30 Hz, 1 H),
7.42–7.52 (m, 2 H), 7.68 (br. s., 1 H), 7.74–7.89 (m, 3 H), 9.41 (d,
J = 2.0 Hz, 1 H); 13C NMR (CDCl3, 125 MHz): d 202.9 (CH),
199.2 (C), 150.7 (CH), 137.3 (C), 133.4 (C), 132.8 (C), 130.0 (CH),
129.2 (CH), 127.7 (CH), 127.6 (CH), 126.6 (two CH), 126.1 (two
CH), 56.2 (CH), 48.1 (CH), 46.5 (CH), 45.0 (CH2), 41.0 (CH),
31.3 (CH2), 25.9 (CH2); MS (m/z, relative intensity): 304 (M+, 89),
276 (6), 233 (7), 184 (20), 165 (27), 141 (100), 128 (31), 115 (13),
95 (15), 69 (12), 55 (24); exact mass calculated for C21H20O2 (M+):
304.1463; found 304.1469.
(1R,2R,4aS,8aR)-1-(4-Bromophenyl)-1,2,3,4,4a,5,6,8a-octa-
hydro-6-oxonaphthalene-2-carbaldehyde (5d). Rf = 0.31 for 5d in
40% EtOAc–hexane, white solid, m.p. 146–148 ◦C, 74% yield.
Selected spectroscopic data for 5d: [a]2D5 +19.6 (c 7.5 CHCl3); IR
(neat): 3030, 2926, 2857, 1721, 1675, 1489, 1256, 1010, 881, 805,
1
766 cm-1; H NMR (CDCl3, 500 MHz): d 1.41–1.54 (m, 2 H),
1.87–1.97 (m, 2 H), 2.01–2.09 (m, 1 H), 2.17–2.26 (m, 1 H), 2.34
(t, J = 10.62 Hz, 1 H), 2.51 (d, J = 16.60 Hz, 1 H), 2.60–2.68 (m,
1 H), 2.70–2.78 (m, 1 H), 5.88 (d, J = 10.01 Hz, 1 H), 6.40 (d, J =
10.25 Hz, 1 H), 7.11 (d, J = 7.57 Hz, 2 H), 7.47 (d, J = 7.57 Hz,
2 H), 9.38 (s, 1 H); 13C NMR (CDCl3, 125 MHz): d 202.3 (CH),
198.9 (C), 150.1 (CH), 147.0 (CH), 139.1 (C), 137.3 (CH), 131.7
(CH), 130.2 (CH), 130.0 (CH), 121.4 (C), 56.3 (CH), 47.1 (CH),
46.3 (CH), 44.8 (CH2), 40.9 (CH), 31.7 (CH2), 25.8 (CH2); MS
(m/z, relative intensity): 332 (M+, 49), 261 (9), 235 (14), 182 (15),
171 (58), 128 (72), 120 (86), 108 (100), 95 (38), 91 (30), 77 (37), 55
(22); exact mass calculated for C17H17BrO2 (M+): 332.0412; found
332.0417.
(1R,2R,4aS,8aR)-1,2,3,4,4a,5,6,8a-Octahydro-7-methyl-6-oxo-
1-phenylnaphthalene-2-carbaldehyde (5h). Rf = 0.6 for 5h in 40%
EtOAc–hexane, white solid, m.p. 107–109 ◦C, 84% yield. Selected
spectroscopic data for 5h: [a]2D5 +57.4 (c 2 CHCl3); IR (neat): 2925,
2895, 1718, 1671, 1541, 1455, 1259, 1070, 1011, 800, 760, 702 cm-1;
1H NMR (CDCl3, 500 MHz): d 1.36–1.53 (m, 2 H), 1.59 (br. s.,
3 H), 1.81–1.92 (m, 2 H), 1.97 (d, J = 13.43 Hz, 1 H), 2.17 (t, J =
15.14 Hz, 1 H), 2.35 (t, J = 10.50 Hz, 1 H), 2.49 (d, J = 16.36 Hz,
1 H), 2.59 (t, J = 11.47 Hz, 1 H), 2.70 (t, J = 11.11 Hz, 1 H),
6.14 (br. s., 1 H), 7.17–7.23 (m, 3 H), 7.28–7.34 (m, 2 H), 9.33
(s, 1 H); 13C NMR (CDCl3, 125 MHz): d 203.2 (CH), 199.2 (C),
145.6 (CH), 140.1 (C), 136.0 (C), 129.0 (two CH), 128.5 (CH),
127.4 (two CH), 56.4 (CH), 48.0 (CH), 46.6 (CH), 45.0 (CH2),
41.2 (CH), 31.0 (CH2), 25.8 (CH2), 15.7 (CH3); MS (m/z, relative
intensity): 268 (M+, 99), 240 (15), 197 (18), 162 (11), 134 (100),
122 (61), 115 (33), 91 (67), 77 (23), 55 (9); exact mass calculated
for C18H20O2 (M+): 268.1463; found 268.1465.
(1R,2R,4aS,8aR)-1,2,3,4,4a,5,6,8a-Octahydro-6-oxo-1-p-toly-
lnaphthalene-2-carbaldehyde (5e). Rf = 0.53 for 5e in 40%
EtOAc–hexane, white solid, m.p. 106–108 ◦C, 72% yield. Selected
spectroscopic data for 5e: [a]2D5 +39.0 (c 2 CHCl3); IR (neat): 3030,
2925, 2857, 1721, 1683, 1515, 1259, 1103, 809, 771 cm-1; 1H NMR
(CDCl3, 500 MHz): d 1.40–1.57 (m, 2 H), 1.86–1.97 (m, 2 H), 2.01
(d, J = 12.70 Hz, 1 H), 2.22 (t, J = 15.14 Hz, 1 H), 2.31 (s, 3 H),
2.36 (t, J = 10.74 Hz, 1 H), 2.51 (d, J = 16.36 Hz, 1 H), 2.60
(t, J = 11.48 Hz, 1 H), 2.73 (t, J = 10.99 Hz, 1 H), 5.86 (d, J =
10.01 Hz, 1 H), 6.47 (d, J = 10.25 Hz, 1 H), 7.06–7.12 (m, 2 H),
7.12–7.17 (m, 2 H), 9.37 (s, 1 H); 13C NMR (CDCl3, 125 MHz):
d 203.2 (CH), 199.2 (C), 150.9 (CH), 137.2 (C), 136.7 (C), 129.8
(CH), 129.7 (CH), 129.6 (CH), 128.2 (two CH), 56.4 (CH), 47.6
(CH), 46.6 (CH), 44.9 (CH2), 41.0 (CH), 31.2 (CH2), 25.8 (CH2),
21.0 (CH3); MS (m/z, relative intensity): 268 (M+, 39), 197 (9), 148
(37), 128 (26), 115 (23), 105 (100), 91 (26), 77 (17), 55 (7); exact
mass calculated for C18H20O2 (M+): 268.1463; found 268.1460.
(1R,2R,4aS,8aR)-1,2,3,4,4a,5,6,8a-Octahydro-7-methyl-1-(4-
nitrophenyl)-6-oxonaphthalene-2-carbaldehyde (5i). Rf = 0.25 for
5i in 40% EtOAc–hexane, white solid, m.p. 164–166 ◦C, 82% yield.
Selected spectroscopic data for 5i: [a]2D5 +55.8 (c 2.5 CHCl3); IR
(neat): 2925, 2858, 1719, 1673, 1519, 1346, 1083, 855, 754, 700 cm-1;
1H NMR (CDCl3, 500 MHz): d 1.48 (br. s., 2 H), 1.63 (br. s., 3 H),
1.94 (br. s., 2 H), 2.14 (br. s., 1 H), 2.17–2.28 (m, 1 H), 2.41 (br. s.,
1 H), 2.56 (d, J = 16.60 Hz, 1 H), 2.82 (d, J = 3.17 Hz, 2 H),
6.02 (br. s., 1 H), 7.44 (br. s., 2 H), 8.22 (br. s., 2 H), 9.40 (d, J =
3.66 Hz, 1 H); 13C NMR (CDCl3, 125 MHz): d 201.4 (CH), 198.7
(C), 148.5 (C), 147.2 (C), 144.1 (CH), 136.9 (C), 129.4 (two CH),
124.2 (two CH), 56.5 (CH), 47.4 (CH), 46.2 (CH), 44.9 (CH2),
41.1 (CH), 31.0 (CH2), 25.7 (CH2), 15.7 (CH3); MS (m/z, relative
intensity): 313 (M+, 100), 271 (15), 242 (21), 216 (11), 165 (11),
141 (26), 134 (44), 115 (42), 91 (27), 69 (42), 55 (15); exact mass
calculated for C18H19NO4 (M+): 313.1314; found 313.1318.
(1R,2R,4aS,8aR)-1,2,3,4,4a,5,6,8a-Octahydro-1-(2-nitrophe-
nyl)-6-oxonaphthalene-2-carbaldehyde (5f). Rf = 0.13 for 5f in
40% EtOAc–hexane, yellow oil, 63% yield. Selected spectroscopic
data for 5f: [a]2D5 +54.3 (c 5.5 CHCl3); IR (neat): 2925, 2855,
1
1717, 1683, 1525, 1354, 1258, 853, 745 cm-1; H NMR (CDCl3,
500 MHz): d 1.43–1.55 (m, 2 H), 1.92–2.06 (m, 2 H), 2.14 (d,
J = 8.30 Hz, 1 H), 2.18–2.27 (m, 1 H), 2.45 (t, J = 10.74 Hz,
1 H), 2.54 (d, J = 16.85 Hz, 1 H), 2.71–2.81 (m, 1 H), 3.39 (t,
J = 11.35 Hz, 1 H), 5.92 (d, J = 10.01 Hz, 1 H), 6.39 (d, J =
10.25 Hz, 1 H), 7.35–7.43 (m, 1 H), 7.45 (d, J = 7.81 Hz, 1 H),
7.56–7.63 (m, 1 H), 7.77 (d, J = 8.06 Hz, 1 H), 9.37 (s, 1 H);
13C NMR (CDCl3, 125 MHz): d 201.2 (CH), 198.6 (C), 151.6 (C),
149.9 (CH), 134.9 (C), 133.1 (CH), 130.3 (CH), 128.2 (CH), 128.15
(CH), 124.3 (CH), 57.0 (CH), 46.6 (CH), 44.8 (CH2), 40.8 (CH),
40.4 (CH), 31.3 (CH2), 25.7 (CH2); MS (m/z, relative intensity):
(1R,2R,4aS,8aR)-1-(4-Bromophenyl)-1,2,3,4,4a,5,6,8a-octahy-
dro-7-methyl-6-oxonaphthalene-2-carbaldehyde (5j). Rf = 0.48
◦
for 5j in 40% EtOAc–hexane, white solid, m.p. 183–185 C, 75%
This journal is
The Royal Society of Chemistry 2009
Org. Biomol. Chem., 2009, 7, 3095–3101 | 3099
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