810
A.A. Kasali et al. / Phytochemistry 59 (2002) 805–810
Hz), 1.82–1.92 (m, 1H, H-10), 2.26–2.35 (m, 1H, H-2a),
2.62–2.70 (m, 1H, H-2b), 4.98 (d, 1H, H-3, J=1.5 Hz);
13C NMR (125.75 MHz, C6D6): ꢀ=16.86 (q, C-15),
20.19 (q, C-14), 21.08 (q, C-13), 21.12 (q, C-12), 23.99 (t,
C-8), 31.88 (d, C-10), 32.73 (s, C-1), 32.98 (t, C-9), 33.85
(d, C-11), 35.28 (d, C-6), 35.86 (d, C-5), 40.53 (t, C-2),
41.16 (d, C-7), 120.73 (d, C-3), 145.20 (s, C-4); MS (EI,
70 eV), m/z (rel. Int.): 39 (16), 41 (46), 43 (16), 55 (24),
77 (20), 79 (28), 81(20), 91(45), 93 (23), 105 (46), 107
(22), 119 (23), 120 (100), 121 (16), 161 (72), 204 (12).
1.48–1.58 (m, 2H, H-2a, H-11), 1.61–1.69 (m, 4H, CH3-
4, H-8b, H-10), 1.88–2.05 (m, 2H, H-2b, H-3b), 2.42 (br.
s, 1H, H-6), 5.20 (br. s, 1H, H-5); 13C NMR (100.6
MHz, C6D6): ꢀ=14.8 (q, C-14), 20.7 (q, C-12), 21.9 (q,
C-13), 23.4 (q, C-15), 26.8 (t, C-8), 28.9 (d, C-11), 29.9
(t, C-3), 30.9 (d, C-10), 31.0 (t, C-9), 35.1( t, C-2), 42.7
(d, C-7), 45.6 (d, C-6), 71.8 (s, C-1), 121.1 (d, C-5), 134.7
(s, C-4); MS (EI, 70 eV), m/z (rel. int.): 39 (36), 41(100),
43 (83), 53 (25), 55 (41), 77 (28), 79 (27), 81(29), 91(35),
93 (26), 105 (33), 119 (25), 161 (45), 179 (77), 204 (12),
222 (2).
3.3.2. 6-epi-ꢂ-Cubebene (3)
2,3,3aa,3bb,4,5,6,7-Octahydro-7-methyl-3-methylene-4-
(1-methylethyl)-1H-cyclopenta[1,3]cyclopropa[1,2]benzene,
colourless oil, RICPSIL5:1449, sense of optical rotation
(benzene): (+) ; 1H NMR (500.1MHz, C 6D6): ꢀ=0.63–
0.72 (m, 1H, H-8a), 0.80–0.90 (m, 1H, H-9a), 0.91 (d,
3H, H-13, J=6.3 Hz), 1.01 (d, 6H, H-12, H-14, J=6.0
Hz), 1.08–1.12 (m, 1H, H-6), 1.36–1.44 (m, 3H, H-7, H-
8b, H-11), 1.44–1.49 (m, 2H, H-5, H-9b), 1.63 (dd, 1 H,
H-2a, J=8.2, 12.0 Hz), 1.73–1.82 (m, 2H, H-2b/H-10),
1.86–1.96 (m, 1H, H-3a), 2.05 (dd, 1H, H-3b, J=9.1,
16.7 Hz), 4.80 (s, 1H, H-15a), 4.99 (s, 1H, H-15b); 13C
NMR (125.8 MHz, C6D6): ꢀ=19.94 (q, C-14), 20.86 (q,
C-12), 20.89 (q, C-13), 23.52 (t, C-8), 27.49 (d, C-6),
29.16 (t, C-3), 31.17 (t, C-2), 31.34 (d, C-10), 32.94 (t, C-
9), 33.44 (d, C-11), 33.93 (d, C-5), 36.00 (s, C-1), 40.72
(d, C-7), 101.46 (t, C-15), 154.47 (s, C-4); MS (EI, 70
eV), m/z (rel. int.): 39 (18), 41 (50), 43 (16), 55 (29), 77
(20), 79 (27), 81 (25), 91 (48), 93 (23), 105 (51), 107 (20),
119 (27), 120 (100), 121 (15), 161 (90), 204 (12).
Acknowledgements
We would like to acknowledge the financial support
from DAAD for A.A. Kasali and of the Fonds der
Chemischen Industrie. We are grateful to Dr. V. Sinn-
well, University of Hamburg, for his support in obtain-
ing the NMR spectra and to Mrs. A. Meiners and Mr.
M. Preusse, University of Hamburg, for their assistance
in the GC–MS investigations.
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1
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J=6.9 Hz), 0.90 (d, 3H, CH3-11, J=6.6 Hz), 0.94 (d,
3H, CH3-11, J=6.4 Hz), 0.90–0.97 (m, 1H, H-8a), 1.19–
1.36 (m, 3H, H-3a, H-7, H-9a), 1.38–1.46 (m, 1H, H-8b),