134
HETEROCYCLES, Vol. 68, No. 1, 2006
9-Ethoxy-3,4,10-trimethoxy-5,14-dihydro-8H-13-oxadibenzo[a,f]cyclodecene (8c)
o
8c (0.37 g, 50%) was obtained as colorless crystals, mp 143 C (EtOAc + n-hexane), Rf = 0.30 (EtOAc:
n-hexane = 1: 5), 1H-NMR (CDCl3, 400 MHz) δ 1.41 (t, J = 7.2 Hz, 3H, OCH2CH3), 3.64 (d, J = 8.0 Hz,
2H, H-8), 3.81 (s, 6H, 2 x OCH3), 3.86 (s, 3H, OCH3), 3.99 (d, J = 8.0 Hz, 2H, H-5), 4.03 (q, J = 7.2 Hz,
2H, OCH2CH3), 4.94 (s, 2H, H-14), 5.49 (dt, J = 10.8, 7.8 Hz,1H, H-6), 5.59 (dt, J = 10.4, 8.2 Hz, 1H,
H-7), 6.72 (d, J = 8.8 Hz, 2H, H-2 and H-11), 6.84 (d, J = 8.8 Hz, 1H, H-12), 6.94 (d, J = 8.0 Hz, 1H,
13
H-1); C-NMR (CDCl3, 100 MHz) δ 15.67 (OCH2CH3), 22.44 (C-8), 24.77 (C-5), 55.62 (OCH3), 56.01
(OCH3), 60.86 (OCH3), 69.24 (OCH2CH3), 75.52 (C-14), 109.06 (C-2), 110.08 (C-11), 115.19 (C-12),
125.41 (C-1), 126.48 (C-6), 127.52 (C-7), 128.53, 128.75, 133.30, 146.24, 147.79, 149.20, 152.25,
153.17; EI-MS (70eV) m/z (rel. intensity, %) 370 (M+, 15), 205 (9), 190 (29), 189 (100), 188 (14), 174
(17), 159 (9.0); HRMS (EI, m/z): Calcd for C22H26O5: 370.1775. Found: 370.1777; Anal. Calcd for
C22H26O5: C, 71.33; H, 7.07. Found: C, 71.59; H, 7.11.
4,9-Diethoxy-3,10dimethoxy-5,14-dihydro-8H-13-oxadibenzo[a,f]cyclodecene (8d)
o
8d (0.31 g, 41%) was obtained as colorless crystals, mp 114 C (EtOAc + n-hexane), Rf = 0.36 (EtOAc:
n-hexane = 1: 5), 1H-NMR (CDCl3, 400 MHz) δ 1.41 (t, J = 7.2 Hz, 3H, OCH2CH3), 3.64 (d, J = 8.0 Hz,
2H, H-8), 3.82 (s, 3H, OCH3), 3.84 (s, 3H, OCH3), 4.00 (q, J = 7.2 Hz, 2H, OCH2CH3), 4.01 (d, J = 8.8
Hz, 2H, H-5), 4.03 (q, J = 7.2 Hz, 2H, OCH2CH3), 4.93 (s, 2H, H-14), 5.48 (dt, J = 10.0, 7.8 Hz, 1H, H-6),
5.57 (dt, J = 10.8, 7.8 Hz, 1H, H-7), 6.71 (d, J = 8.4 Hz, 1H, H-2), 6.72 (d, J = 8.8 Hz, 1H, H-11), 6.85 (d,
J = 8.8 Hz, 1H, H-12), 6.93 (d, J = 8.4 Hz, 1H, H-1); 13C-NMR (CDCl3, 100 MHz) δ 15.63 (OCH2CH3),
15.68 (OCH2CH3), 22.49 (C-8), 24.95 (C-5), 55.64 (OCH3), 56.02 (OCH3), 69.04 (OCH2CH3), 69.29
(OCH2CH3), 75.82 (C-14), 108.98 (C-2), 110.05 (C-11), 115.45 (C-12), 125.23 (C-1), 126.51 (C-6),
127.45 (C-7), 128.65, 128.71, 133.39, 146.21, 146.86, 149.23, 152.43, 153.30; EI-MS (70eV) m/z (rel.
intensity, %) 384 (M+, 22), 207 (12), 205 (14), 204 (32), 203 (100), 202 (21), 190 (9), 176 (11), 175 (23),
143 (18), 115 (8); HRMS (EI, m/z): Calcd for C23H28O5: 384.1931. Found: 384.1934; Anal. Calcd for
C23H28O5: C, 71.85; H, 7.34. Found: C, 71.87; H, 7.34.
9-Ethoxy-4-isopropyl-3,10-dimethoxy-5,14-dihydro-8H-13-oxadibenzo[a,f]cyclodecene (8e)
o
8e (0.37 g, 47%) was obtained as colorless crystals, mp 132 C (EtOAc + n-hexane), Rf = 0.39 (EtOAc:
n-hexane = 1: 5), 1H-NMR (CDCl3, 400 MHz) δ 1.31 (d, J = 6.0 Hz, 6H, OCH(CH3)2), 1.41 (t, J = 7.2 Hz,
3H, OCH2CH3), 3.64 (d, J = 8.4 Hz, 2H, H-8), 3.82 (s, 3H, OCH3), 3.83 (s, 3H, OCH3), 4.03 (q, J = 7.2
Hz, 2H, OCH2CH3), 4.05 (d, J = 8.4 Hz, 2H, H-5), 4.42 (setp, J = 6.0 Hz, 1H, OCH(CH3)2), 4.91 (s, 2H,
H-14), 5.44 (dt, J = 10.4, 7.6 Hz, 1H, H-6), 5.56 (dt, J = 10.4, 8.0 Hz, 1H, H-7), 6.70 (d, J = 8.4 Hz, 1H,
H-2), 6.73 (d, J = 8.8 Hz, 1H, H-11), 6.86 (d, J = 8.8 Hz, 1H, H-12), 6.91 (d, J = 8.4 Hz, 1H, H-1);
13C-NMR (CDCl3, 100 MHz) δ 15.63 (OCH2CH3), 22.45 OCH(CH3)2), 22.50 (C-8), 25.26 (C-5), 55.55