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6351
3H, Me0), 3.22 (bd, 1H, J¼7.5 Hz, H-1), 3.38 (bt, 1H,
J¼7.8 Hz, H-6), 3.59–3.61 (m, 2H, H-5, H-9), 5.54–5.56
(m, 1H, H-4), 5.74 (d, 1H, J¼10.9 Hz, H-11), 5.97 (t, 1H,
J¼7.8 Hz, H-8), 6.22 (t, 1H, J¼7.8 Hz, H-7), 6.39 (dd, 1H,
J¼2.1, 5.7 Hz, H-3), 7.10 (dd, 1H, J¼8.7, 10.9 Hz, H-12);
MS m/z212 (Mþ); HRMS: calcd for C15H16O: 212.1201;
found: 212.1195.
3.76 (bs, 4H, H-5, –CO2Me), 3.98 (bd, 1H, J¼8.3 Hz, H-7),
5.64 (t, 1H, J¼8.2 Hz, H-9), 5.81 (d, 1H, J¼11.9 Hz, H-12),
6.02 (t, 1H, J¼8.3 Hz, H-8), 6.61 (dd, 1H, J¼8.5, 11.9 Hz,
H-11), 7.21–7.22 (m, 1H, Ph), 7.28–7.31 (m, 2H, Ph),
7.37–7.39 (m, 2H, Ph); MS m/z 416 (Mþ); HRMS: calcd for
C26H24O5: 416.1624; found: 416.1629.
3.5.10. Compound 27f. 1H NMR d 2.14 (s, 3H, Me), 3.37–
3.41 (m, 2H, H-1, H-6), 3.64 (bd, 1H, J¼7.1 Hz, H-5), 3.76
(bd, 1H, J¼7.4 Hz, H-9), 5.58–5.59 (m, 1H, H-4), 5.80 (d,
1H, J¼11.0 Hz, H-11), 6.04 (t, 1H, J¼7.4 Hz, H-8), 6.24–
6.27 (m, 2H, H-3, H-7), 7.10 (dd, 1H, J¼8.6, 11.0 Hz, H-
12), 7.13–7.17 (m, 3H, Ph), 7.26–7.30 (m, 2H, Ph); MS
m/z274 (Mþ); HRMS: calcd for C20H18O: 274.1358; found:
274.1351.
1
3.5.4. Compound 22e. H NMR d 0.49 (d, 3H, J¼6.8 Hz,
–CHMeMe00), 0.86 (d, 3H, J¼6.8 Hz, –CHMeMe00), 1.07 (s,
3H, Me0), 1.83 (d, 1H, J¼6.7 Hz, H-5), 1.86–1.93 (m, 1H,
–CHMeMe00), 2.16 (d, 1H, J¼6.7 Hz, H-5), 3.19 (t, 1H,
J¼8.3 Hz, H-10), 3.70 (s, 3H, –CO2Me), 3.74–3.77 (m, 4H,
H-7, –CO2Me), 5.88 (t, 1H, J¼8.7 Hz, H-8), 5.93 (d, 1H,
J¼11.9 Hz, H-12), 6.24 (bt, 1H, J¼8.7 Hz, H-9), 6.49 (bs,
1H, H-3), 6.81 (dd, 1H, J¼8.5, 11.9 Hz, H-11); MS m/z382
(Mþ); HRMS: calcd for C23H26O5: 382.1780; found:
382.1771.
3.5.11. Compound 27d. 1H NMR d 3.26–3.31 (m, 2H, H-6,
H-9), 3.60–3.63 (m, 1H, H-5), 3.80 (bd, 1H, J¼7.1 Hz,
H-1), 5.64 (bd, 1H, J¼10.9 Hz, H-11), 5.81 (dd, 1H, J¼2.4,
5.7 Hz, H-4), 5.96 (t, 1H, J¼7.9 Hz, H-8), 6.27 (t, 1H,
J¼7.9 Hz, H-7), 6.38 (dd, 1H, J¼2.4, 5.7 Hz, H-3), 7.04
(dd, 1H, J¼8.7, 10.9 Hz, H-12); 7.07–7.18 (m, 5H, Ph),
7.18–7.34 (m, 5H, Ph0); MS m/z 336 (Mþ); HRMS: calcd
for C25H20O: 336.1514; found: 336.1502.
3.5.5. Compound 25e. 1H NMR d 0.92 (s, 3H, Me0), 0.95 (d,
3H, J¼6.900Hz, –CHMeMe00), 1.02 (d, 3H, J¼060 .9 Hz,
–CHMeMe ), 2.10–2.15 (m, 3H, H-4, –CHMeMe ), 3.19
(t, 1H, J¼8.3 Hz, H-10), 3.62 (bs, 1H, H-5), 3.72 (s, 3H,
–CO2Me), 3.73 (s, 3H, –CO2Me), 3.85–3.88 (m, 2H, H-3,
H-7), 5.68 (d, 1H, J¼11.9 Hz, H-12), 6.03 (t, 1H, J¼8.9 Hz,
H-8), 6.17 (t, 1H, J¼9.1 Hz, H-9), 6.43 (dd, 1H, J¼8.5,
11.9 Hz, H-11); MS m/z 382 (Mþ); HRMS: calcd for
C23H26O5: 382.1780; found: 382.1765.
3.5.12. Compound 29d. 1H NMR d 3.02 (t, 1H, J¼7.9 Hz,
H-6), 3.45–3.48 (m, 2H, H-1, H-9), 3.62 (bd, 1H, J¼7.4 Hz,
H-5), 5.66 (dd, 1H, J¼11.0 Hz, H-11), 5.91 (dd, 1H, J¼2.5,
5.6 Hz, H-2), 5.98 (t, 1H, J¼7.9 Hz, H-8), 6.27 (t, 1H,
J¼7.9 Hz, H-7), 6.34 (dd, 1H, J¼1.6, 5.6 Hz, H-3), 6.70
(dd, 1H, J¼7.9, 11.0 Hz, H-12); 7.09–7.25 (m, 5H, Ph0),
7.25–7.40 (m, 5H, Ph); MS m/z 336 (Mþ); HRMS: calcd for
C25H20O: 336.1514; found: 336.1501.
3.5.6. Compound 27e. 1H NMR d 0.92–0.98 (m, 6H,
00
–CHMeMe ), 1.67 (s, 3H, Me0), 2.79–2.85 (m, 1H,
00
–CHMeMe ), 3.19 (bd, 1H, J¼7.5 Hz, H-1), 3.37 (bt, 1H,
J¼7.8 Hz, H-6), 3.56–3.58 (m, 2H, H-5, H-9), 5.52–5.54
(m, 1H, H-4), 5.76 (d, 1H, J¼10.9 Hz, H-11), 5.95–6.01 (m,
1H, H-8), 6.21 (t, 1H, J¼7.8 Hz, H-7), 6.46 (dd, 1H, J¼2.0,
5.7 Hz, H-3), 7.10 (dd, 1H, J¼8.7, 10.9 Hz, H-12); MS m/z
240 (Mþ); HRMS: calcd for C17H20O: 240.1514; found:
240.1504.
Acknowledgements
We are grateful to the National Science Council of the
Republic of China for financial support of this research.
3.5.7. Compound 27e0. 1H NMR d 0.92–0.98 (m, 3H,
–CHMeMe00), 1.07 (d, 3H, J¼6.8 Hz, –CHMe0Me), 1.61 (s,
3H, Me), 2.71–2.77 (m, 1H, –CHMe0Me00), 3.25 (bd, 1H,
J¼7.5 Hz, H-1), 3.37 (bt, 1H, J¼7.8 Hz, H-6), 3.56–3.58
(m, 2H, H-5) 3.50 (d, 1H, J¼7.4 Hz, H-9), 5.55–5.57 (m,
1H, H-4), 5.76 (d, 1H, J¼10.9 Hz, H-11), 5.95–6.01 (m,
1H, H-8), 6.21 (t, 1H, J¼7.8 Hz, H-7), 6.38 (dd, 1H, J¼2.1,
5.7 Hz, H-3), 7.10 (dd, 1H, J¼8.7, 10.9 Hz, H-12); MS m/z
240 (Mþ); HRMS: calcd for C17H20O: 240.1514; found:
240.1504.
References
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Soc., Chem. Commun. 1987, 1375.
3.5.8. Compound 22f. 1H NMR d 1.59 (s, 3H, Me), 2.01 (d,
1H, J¼6.8 Hz, H-5), 2.31 (d, 1H, J¼6.8 Hz, H-5), 3.56 (s,
3H, –CO2Me), 3.79 (m, 3H, –CO2Me), 3.81–3.85 (m, 2H,
H-4, H-10), 3.92 (d, 1H, J¼8.3 Hz, H-7), 5.68 (t, 1H,
J¼9.5 Hz, H-8), 5.87 (bt, 1H, J¼9.5 Hz, H-9), 6.04 (d, 1H,
J¼11.5 Hz, H-12), 6.86 (bd, 1H, J¼2.8 Hz, H-3), 6.96 (dd,
1H, J¼8.5, 11.5 Hz, H-11), 7.04–7.06 (m, 2H, Ph), 7.11–
7.13 (m, 1H, Ph), 7.15–7.18 (m, 2H, Ph); MS m/z416 (Mþ);
HRMS: calcd for C26H24O5: 416.1624; found: 416.1629.
4. Machiguchi, T.; Hasegawa, T.; Ishii, Y.; Yamabe, S.; Minato,
T. J. Am. Chem. Soc. 1993, 115, 11536.
5. Kitahara, Y.; Oda, M. In Jerusalem Symposia on Quantum
Chemistry and Biochemistry. Aromaticity, Pseudo-
Aromaticity, Antiaromaticity; Bergman, D., Pullman, B.,
Eds.; Academic: New York, 1971; Vol. 3, p 284.
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1970, 92, 6392.
7. Bhacca, N. S.; Luskus, L. J.; Houk, K. N. Chem. Commun.
1971, 109.
1
3.5.9. Compound 25f. H NMR d 1.40 (s, 3H, Me), 2.22
(bd, 1H, J¼6.9 Hz, H-4), 2.36 (bd, 1H, J¼6.9 Hz, H-4),
8. Houk, K. N.; Luskus, L. J.; Bhacca, N. S. Tetrahedron Lett.
1972, 22, 2297.
3.30 (t, 1H, J¼8.6 Hz, H-10), 3.70 (bs, 4H, H-3, –CO2Me),