J. A. Wright et al. / Tetrahedron Letters 42 (2001) 4033–4036
4035
136.1, 133.7, 133.5, 128.9, 128.8, 128.7, 128.4, 128.2,
128.1, 127.3, 127.1, 126.6, 126.5, 126.4, 126.4, 126.3,
99.0, 78.1, 76.4, 74.2, 73.4, 70.2, 68.9, 68.8, 55.8;
HRMS (EI+) calcd for C36H36O6 (M+) 564.251 18,
CDCl3): l 7.78 (t, 2H, J=5.0 Hz, ArH), 7.71 (d, 2H,
J=7.6 Hz, ArH), 7.51 (br s, 1H, ArH), 7.44 (m, 2H,
ArH), 7.35–7.24 (m, 10H, ArH), 7.20 (d, 2H, J=8.4
Hz, ArH), 6.77 (d, 2H, J=8.4 Hz, ArH), 4.98 (d, 1H,
J=11.2 Hz), 4.93 (d, 1H, J=11.2 Hz), 4.81 (d, 1H,
J=11.2 Hz), 4.78 (d, 1H, J=12.0 Hz), 4.65 (d, 1H,
J=12.0 Hz), 4.62 (d, 1H, J=3.6 Hz), 4.55 (d, 1H,
J=12.0 Hz), 4.55 (d, 1H, J=11.2 Hz), 4.35 (d, 1H,
J=12.0 Hz), 3.98 (dd, 1H, J=9.2 Hz, 9.2 Hz), 3.67 (s,
3H, MeO), 3.76–3.67 (m, 3H), 3.60 (dd, 1H, J=10.0
Hz, 9.4 Hz), 3.56 (dd, 1H, J=9.6 Hz, 3.6 Hz), 3.37 (s,
3H, MeO); 13C NMR (100 MHz, CDCl3): l 159.6,
139.3, 138.6, 136.2, 133.6, 133.3, 130.3, 130.0, 128.8,
128.8, 128.5, 128.4, 128.3, 128.0, 127.9, 126.8, 126.4,
126.2, 114.1, 98.7, 82.6, 80.2, 78.0, 76.1, 75.4, 73.8, 73.5,
70.5, 68.3, 55.6, 55.5; HRMS (EI+) calcd for
C40H42O7Na (M++Na) 657.282 82, found 657.285 00.
1
found 564.251 25. Compound 19: H NMR (400 MHz,
CDCl3) l 7.88–7.68 (m, 8H, ArH), 7.54 –7.40 (m, 6H,
ArH), 7.38–7.23 (m, 5H, ArH), 7.16 (d, 2H, J=8.4 Hz,
ArH), 6.72 (d, 2H, J=8.4 Hz, ArH), 5.01 (d, 1H,
J=12.4 Hz), 4.97 (d, 1H, J=12.8 Hz), 4.90–4.86 (m,
3H), 4.71 (d, 1H, J=4.0 Hz), 4.54 (d, 1H, J=11.6 Hz),
4.48 (d, 1H, J=12.0 Hz), 4.38 (d, 1H, J=12.0 Hz), 4.11
(dd, 1H, J=10.0 Hz, 4.0 Hz), 4.00 (dd, 1H, J=10.0 Hz,
2.4 Hz), 3.95 (br, 1H), 3.89 (t, 1H, J=6.4 Hz), 3.73 (s,
3H), 3.49 (d, 2H, J=6.4 Hz), 3.37 (s, 3H, MeO); 13C
NMR (100 MHz, CDCl3): l 138.5, 136.8, 136.4, 133.8,
133.7, 133.5, 133.4, 131.2, 130.3, 129.0, 128.8, 128.5,
128.4, 128.3, 128.2, 128.1, 128.1, 127.4, 127.3, 126.6,
126.5, 126.5, 126.4, 126.2, 126.1, 114.4, 114.0, 99.2,
79.5, 76.4, 75.3, 74.8, 74.0, 74.0, 73.9, 69.8, 69.7, 56.1,
55.8, 55.6; HRMS (EI+) calcd for C44H44O7Na (M++
1
Compound 8: H NMR (400 MHz, CDCl3): l 7.83–
7.75 (m, 4H, ArH), 7.47–7.43 (m, 3H, ArH), 7.29 (d,
2H, J=8.4 Hz, ArH), 7.25 (d, 2H, J=8.4 Hz, ArH),
7.19–7.13 (m, 3H, ArH), 7.01 (m, 2H, ArH), 6.87 (d,
2H, J=8.4 Hz, ArH), 6.84 (d, 2H, J=8.4 Hz, ArH),
4.89 (d, 1H, J=10.8 Hz), 4.81 (d, 1H, J=11.2 Hz), 4.76
(d, 1H, J=12.0 Hz), 4.74 (d, 1H, J=12.0 Hz), 4.73 (d,
1H, J=10.8 Hz), 4.62 (d, 1H, J=12.0 Hz), 4.60 (d, 1H,
J=12.4 Hz), 4.58 (d, 1H, J=3.2 Hz), 4.42 (d, 1H,
J=11.2 Hz), 3.95 (dd, 1H, J=10.0 Hz, 9.2 Hz), 3.80 (s,
3H, MeO), 3.79 (s, 3H, MeO), 3.73–3.58 (m, 5H), 3.53
(dd, 1H, J=10.0 Hz, 3.6 Hz), 3.37 (s, 3H, MeO); 13C
NMR (100 MHz, CDCl3): l 159.8, 159.6, 138.6, 135.8,
133.6, 133.4, 131.5, 130.8, 130.1, 130.0, 129.4, 128.6,
128.6, 128.3, 128.1, 127.9, 127.1, 126.5, 126.4, 126.3,
114.3, 114.2, 98.7, 82.3, 80.0, 78.1, 75.8, 75.4, 74.0, 73.4,
70.5, 68.9, 55.7, 55.7, 55.6; HRMS (EI+) calcd for
C41H44O8Na (M++Na) 687.293 39, found 687.292 90.
1
Na) 707.298 47, found 707.297 40. Compound 20: H
NMR (400 MHz, CDCl3): l 7.40–7.24 (m, 5H), 4.83 (d,
1H, J=4.0 Hz), 4.59 (s, 2H), 4.07 (br s, 1H), 3.90 (t,
1H, J=4.8 Hz), 3.83 (td, 1H, J=9.2 Hz, 3.6 Hz),
3.80–3.73 (m, 2H), 3.74–3.70 (m, 1H), 3.42 (s, 3H), 2.91
(d, 1H, J=2.0 Hz, OH), 2.56 (d, 1H, J=5.6 Hz), 2.02
(d, 1H, J=9.6 Hz); 13C NMR (100 MHz, CDCl3): l
138.0, 128.9, 128.3, 128.1, 99.9, 74.3, 71.8, 70.5, 70.4,
70.2, 69.2, 56.0; HRMS (EI+) calcd for C14H20O6Na
(M++Na) 307.115 76, found 307.117 30. Compound 23:
1H NMR (400 MHz, CDCl3) l 7.85–7.60, 7.50–7.20 (m,
17H, ArH), 7.10 (d, 2H, J=8.4 Hz, ArH), 6.78 (d, 2H,
J=8.4 Hz, ArH), 5.06 (d, 1H, J=11.2 Hz), 4.84 (dd,
2H, J=12.0, 6.8 Hz), 4.74–4.67 (m, 4H), 4.40–4.37 (dd,
2H, Jgem=11.6 Hz, ABq), 4.06 (dd, 1H, J=10.0, 3.6
Hz), 3.98–3.86 (m, 3H), 3.94 (s, 3H, MeO), 3.54–3.47
(m, 2H), 3.36 (s, 3H, MeO); 13C NMR (100 MHz,
CDCl3): l 139.0, 136.5, 133.4, 130.4, 129.8, 128.8,
128.7, 128.5, 128.3, 128.0, 127.9, 127.9, 127.3, 126.8,
126.4, 126.3, 114.2, 99.3, 79.6, 77.0, 75.5, 75.1, 74.1,
73.8, 73.6, 69.6, 69.1, 55.8, 55.7; HRMS (EI+) calcd for
C40H42O7 (M+) 634.293 05, found 634.295 95.
1
Compound 12: H NMR (400 MHz, CDCl3): l 7.83–
7.71 (m, 8H, ArH), 7.51–7.44 (m, 6H, ArH), 7.25–7.22
(m, 5H, ArH), 7.11–7.09 (m, 2H, ArH), 6.82 (d, 2H,
J=8.4 Hz, ArH), 5.16 (d, 1H, J=11.2 Hz), 4.99 (d, 1H,
J=11.2 Hz), 4.95 (d, 1H, J=12.4 Hz), 4.86 (d, 1H,
J=12.4 Hz), 4.83 (d, 1H, J=11.2 Hz), 4.67 (d, 1H,
J=3.6 Hz), 4.55 (d, 1H, J=11.6 Hz), 4.45 (d, 1H,
J=11.6 Hz), 4.39 (d, 1H, J=11.6 Hz), 4.06 (dd, 1H,
J=9.4 Hz, 9.4 Hz), 3.81–3.76 (m, 1H), 3.74 (s, 3H,
MeO), 3.70 (dd, 1H, J=10.0 Hz, 3.6 Hz), 3.65 (d, 1H,
J=9.4 Hz), 3.65 (dd, 1H, J=9.4 Hz, 3.6 Hz), 3.60 (dd,
1H, J=10.4 Hz, 2.0 Hz), 3.40 (s, 3H, MeO); 13C NMR
(100 MHz, CDCl3): l 157.4, 136.5, 134.6, 133.8, 131.5,
131.4, 131.3, 131.1, 128.1, 127.8, 127.6, 126.5, 126.2,
126.1, 125.9, 125.8, 125.8, 125.2, 124.6, 124.3, 124.2,
124.1, 124.1, 123.9, 111.9, 96.4, 80.3, 78.0, 75.9, 73.9,
73.2, 71.6, 71.3, 68.3, 66.1, 53.4, 53.4; HRMS (EI+)
calcd for C44H44O7Na (M++Na) 707.298 47, found
707.301 40. Compound 18: 1H NMR (400 MHz,
CDCl3): l 7.95–7.75 (m, 8H, ArH), 7.64–7.48 (m, 6H,
ArH), 7.40–7.28 (m, 5H, ArH), 5.04–4.88 (m, 4H), 4.76
(d, 1H, J=2.8 Hz), 4.59 (dd, 2H, Jgem=11.6, ABq),
4.12 (br s, 1H), 4.03 (dd, 1H, J=10.0 Hz, 3.6 Hz), 3.98
(dd, 1H, J=10.0 Hz, 2.8 Hz), 3.94 (t, 1H, J=5.2 Hz),
3.77 (dd, 1H, J=10.0 Hz, 5.2 Hz), 3.71 (dd, 1H,
J=10.0 Hz, 5.8 Hz), 3.43 (s, 3H, MeO), 2.79 (br s, 1H,
OH); 13C NMR (100 MHz, CDCl3): l 138.5, 136.3,
Acknowledgements
The authors wish to thank the BBRSC (J.A.W.) and
the Royal Society (J.B.S.) for funding, and St. John’s
College, Cambridge (J.-Q. Yu) for a research fellow-
ship.
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E. A.; Gaunt, M. J.; Yu, J.; Spencer, J. B. Org. Lett. 2000,
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