10172
A. Padwa, A. G. Waterson / Tetrahedron 56 (2000) 10159±10173
10. Padwa, A.; Gunn, D. E.; Osterhout, M. H. Synthesis 1997,
1353.
dried over MgSO4. The solvent was removed under reduced
pressure and the residue was subjected to silica gel chroma-
tography to give 0.02 g (55%) of 47 as a white solid: mp
175±1778C (lit.56 mp 175±1778C); IR (CHCl3) 3052, 1650,
11. Grierson, D. S.; Husson, H. P. In Comprehensive Organic
Synthesis, Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford,
1991; Vol. 6, pp 909±947.
1
and 1451 cm21; H NMR (CDCl3, 400 MHz) d 2.83±2.89
12. Kennedy, M.; McKervey, M. A. In Comprehensive Organic
Synthesis, Trost, B. M., Fleming, I. Eds.; Pergamon: Oxford, 1991;
Vol. 7, pp 193±216.
(m, 1H), 2.90±3.00 (m, 3H), 3.10±3.15 (m, 1H), 4.70±5.10
(m, 2H), 5.93 (s, 2H), 6.76 (s, 1H), 6.78 (s, 1H), 7.25±7.65
(m, 3H), and 8.07 (d, 1H, J8.0 Hz); 13C NMR (CDCl3,
100 MHz) d 29.7, 33.5, 42.0, 49.4, 100.9, 107.3, 107.5,
117.3, 124.6, 126.4, 126.5, 126.8, 127.1, 127.9, 128.7,
126.0, 147.0, and 162.2; Anal. Calcd for C18H15NO3: C,
73.69; H, 5.16; N, 4.78. Found: C, 73.52; H, 5.13; N, 4.65.
13. Tamura, Y.; Uenishi, J. I.; Maeda, H.; Choi, H. D.; Ishibashi,
H. Synthesis 1981, 534; Tamura, Y.; Maeda, H.; Akai, S.;
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Acknowledgements
This research was supported by the National Institutes of
Health (GM60003-01) and the National Science Founda-
tion. We thank Bethy Jaskal for some experimental
assistance.
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