576
X. Fu et al. / Tetrahedron Letters 43 (2002) 573–576
3. Bolm, C.; Hildebrand, J. P.; Rudolph, J. Synthesis 2000,
Found: 181.0862. Elemental analysis: calcd for C10H12O3,
C, 66.65; H, 6.71. Found: C, 66.76; H, 6.70.
For compound 4: H NMR (CDCl3): 7.53 (d, 2H, J=7.8
911.
1
4. Schio, L.; Chatreaux, F.; Klich, M. Tetrahedron Lett.
2000, 41, 1543.
Hz), 7.38 (m, 3H), 7.03 (d, 1H, J=16.2 Hz), 6.91 (d, 1H,
J=16.3 Hz), 6.10 (s, 1H), 2.64 (t, 2H, J=6.0 Hz), 2.49 (t,
2H, J=6.2 Hz), 2.12 (m, 2H). 13C NMR (CDCl3): 200.6,
157.4, 136.4, 135.6, 129.8, 129.5, 129.3, 128.6, 127.7, 38.1,
25.4, 22.7.
5. Huffman, M. A.; Yasuda, N. Synlett 1999, 471.
6. (a) Chackalamannil, S.; Davies, R. J.; Wang, Y.;
Asberom, T.; Doller, D. J. Org. Chem. 1999, 64, 1932; (b)
Chackalamannil, S.; Davies, R. J.; Asberom, T.; Doller,
D.; Leone, D. J. Org. Chem. 1999, 64, 1932.
7. Kowalski, C. J.; Fields, K. W. J. Org. Chem. 1981, 46,
197.
8. Thomas, J. B.; Mascarella, W.; Rothman, R. B.; Partilla,
J. S.; Xu, H.; McCullough, K. B.; Dersch, C. M.;
Cantrell, B. E.; Zimmerman, D. M.; Carroll, F. I. J. Med.
Chem. 1998, 41, 1980.
9. Piers, E.; Nagakura, I. Synth. Commun. 1975, 5, 193.
10. De Meijere, A.; Meyer, F. E. Angew. Chem., Int. Ed.
Engl. 1994, 33, 2379.
11. (a) Amatore, C.; Jutand, A. J. Organomet. Chem. 1999,
576, 254; (b) Amatore, C.; Jutand, A. Acc. Chem. Res.
2000, 33, 314; (c) Amatore, C.; Carre, E.; Jutand, A.;
M’Barki, M. Organometallics 1995, 14, 1818.
12. Tamura, Y.; Yakura, T.; Terashi, H.; Haruta, J.; Kita, Y.
Chem. Pharm. Bull. 1987, 35, 570.
For compound 5: 1H NMR (CDCl3): 7.16 (dd, 1H,
J=16.5, 0.4 Hz), 6.15 (s, 1H), 5.78 (dd, 1H, J=16.5, 0.5
Hz), 2.48 (m, 4H), 2.13 (m, 2H). 13C NMR (CDCl3):
199.5, 152.3, 151.0, 133.3, 117.3, 102.8, 37.9, 24.4, 22.2.
1
For compound 6: H NMR (DMSO): 7.74 (s, 1H), 7.29
(s, 1H), 7.17 (d, 1H, J=15.8 Hz), 6.52 (d, 1H, J=15.7
Hz), 6.13 (s, 1H), 2.46 (t, 2H, J=5.8 Hz), 2.36 (t, 2H,
J=6.2 Hz), 1.97 (m, 2H). 13C NMR (DMSO): 200.1,
166.7, 156.0, 140.3, 131.4, 129.3, 38.1, 25.2, 22.6.
For compound 7: 1H NMR (CDCl3): 7.19 (d, 1H, J=
16.2 Hz), 6.49 (d, 1H, J=16.2 Hz), 6.21 (s, 1H), 2.49 (m,
4H), 2.37 (s, 3H), 2.10 (m, 2H). 13C NMR (CDCl3):
199.9, 198.2, 154.5, 143.2, 133.5, 132.3, 38.1, 28.1, 25.2,
22.4.
For compound 8: 1H NMR (DMSO): 12.71 (broad s,
1H), 7.34 (d, 1H, J=15.9 Hz), 6.33 (d, 1H, J=15.9 Hz),
6.23 (s, 1H), 2.51 (t, 2H, J=6.0 Hz), 2.36 (t, 2H, J=6.7
Hz), 1.96 (m, 2H). 13C NMR (DMSO): 200.2, 167.7,
155.4, 144.8, 132.5, 126.1, 38.1, 25.0, 22.6.
13. (a) Comasseto, J. V.; Lo, W. L.; Petragnani, N. Tetra-
hedron 1997, 53, 7445; (b) Wenkert, E.; Schorp, M. K. J.
Org. Chem. 1994, 59, 1943.
14. Overall isolated yield from the corresponding dione. 1H
and 13C NMR spectra for compounds 2, 3, 4, 5, 6, 7, 8,
9 and 10 are summarized below.
For compound 9: 1H NMR (CDCl3): 7.75 (dd, 2H,
J=6.6, 1.7 Hz), 7.31 (d, 2H, J=8.0 Hz), 5.70 (t, 1H,
J=1.2 Hz), 2.40 (s, 3H), 2.32 (d, 2H, J=1.2 Hz), 2.13 (s,
2H), 0.96 (s, 6H). 13C NMR (CDCl3): 199.2, 167.1, 146.6,
132.8, 130.5, 128.7, 116.4, 50.9, 42.9, 33.3, 28.4, 22.2.
For compound 10: 1H NMR (CDCl3): 7.42 (d, 1H,
J=15.9 Hz), 6.29 (d, 1H, J=15.9 Hz), 6.20 (s, 1H), 3.82
(s, 3H), 2.37 (s, 2H), 2.34 (s, 2H), 1.15 (s, 6H). 13C NMR
(CDCl3): 200.2, 166.7, 151.9, 145.1, 132.0, 123.9, 52.4,
51.7, 33.7, 28.7. HRMS (M+1) calcd for C12H17O3,
209.1178, Found: 209.1178. Elemental analysis: calcd for
C12H16O3, C, 69.21; H, 7.74. Found: C, 69.18; H, 7.70.
For compound 2: 1H NMR (CDCl3): 7.83 (doublet of
triplet, 1H, J=8.5, 1.8 Hz), 7.39 (d, 2H, J=8.0 Hz), 5.80
(t, 1H, J=1.2 Hz), 2.49 (m, 5H), 2.32 (t, 2H, J=6.4 Hz),
2.00 (m, 2H). 13C NMR (CDCl3): 199.1, 168.7, 146.6,
132.8, 130.6, 128.6, 117.2, 36.8, 29.0, 22.2, 21.2.
For compound 3: 1H NMR (CDCl3): 7.35 (d, 1H, J=
16.0 Hz), 6.25 (d, 1H, J=16.0 Hz), 6.15 (s, 1H), 3.80 (s,
3H), 2.47 (m, 4H), 2.10 (m, 2H). 13C NMR (CDCl3):
199.5, 166.2, 153.6, 144.5, 132.6, 123.7, 52.0, 37.6, 24.7,
22.0. HRMS (M+1), calcd for C10H13O3, 181.0865.