3160
Acknowledgements
We are grateful to the Department of Science and Technology, New Delhi, for financial support.
References
1. Gilman, H.; Morton, J. W. Org, React. 1954, 8, 258.
2. (a) Gschwend, H. W.; Rodriguez, H. R. Org. React. 1979, 26, 1; (b) Beak, P.; Snieckus, V. Acc. Chem. Res. 1982, 15, 306;
(c) Snieckus, V. Chem. Rev. 1990, 90, 879.
3. (a) Beak, P.; Brown, R. A. J. Org. Chem. 1977, 42, 1823; (b) Clark, R. D.; Repke, D. B.; Kilpatrick, A. T.; Brown, C. M.;
Mackinnon, A. C.; Clague, R. U.; Spedding, M. J. Med. Chem. 1989, 32, 2036; (c) De Silva, S. O.; Reed, J. N.; Billedeau,
R. J.; Wang, X.; Norris, D. J.; Snieckus, V. Tetrahedron 1992, 48, 4863.
4. (a) Jorgenson, M. J. Org. React. 1970, 18, 1; (b) Ahn, T.; Cohen, T. Tetrahedron Lett. 1994, 203.
5. (a) Davies, G. M.; Davies, P. S. Tetrahedron Lett. 1972, 3507; (b) Knight, D. W.; Nott, A. P. J. Chem. Soc., Perkin Trans. 1
1981, 1125; (c) Knight, D. W.; Nott, A. P. ibid 1983, 791; (d) Gammill, R. B.; Hyde, B. R. J. Org. Chem. 1983, 48, 3863;
(e) Carpenter, A. J.; Chadwick, D. J. Tetrahedron Lett. 1985, 1777.
6. Florence, M.; Francois, T.; Queguiner, G. Tetrahedron Lett. 1999, 5483.
7. Mortier, J.; Moyroud, J.; Bennetau, B.; Cain, P. A. J. Org. Chem. 1992, 59, 4042.
8. Maggi, R.; Schlosser, M. J. Org. Chem. 1996, 61, 5430.
9. (a) Katsoulos, G.; Schlosser, M. Tetrahedron Lett. 1993, 6263; (b) Schlosser, M. Angew. Chem., Int. Ed. 1998, 110, 1496.
10. Compound 4: 1H NMR (CDCl3): 0.95 (t, J=7.5 Hz, 3H), 1.40 (m, 2H), 1.65 (m, 2H), 2.92 (t, J=7.2 Hz, 2H), 3.83 (s, 6H),
6.65 (t, J=2.0 Hz, 1H), 7.12 (d, J=2.0 Hz, 2H).
11. Methyl ester of compound 5: mp 151.6–152.8°C; 1H NMR (CDCl3): 3.46 (s, 6H), 3.92 (s, 3H), 7.25 (m, 12H).
12. Methyl ester of compound 6: mp 99–101°C; 1H NMR (CDCl3): 1.37 (t, J=7.1 Hz, 3H), 3.86 (s, 6H), 3.92 (s, 3H), 4.42 (q,
J=7.1 Hz, 2H), 7.24 (s, 2H).
13. Methyl ester of compound 7: mp 71–73°C; 1H NMR (CDCl3): 3.82 (s, 6H), 3.92 (s, 3H), 5.07 (dt, J1=7.0, J2=1 Hz, 1H),
5.19 (dt, J1=11, J2=1 Hz, 1H), 5.30 (s, OH), 5.65 (m, 1H), 6.13 (m, 1H), 7.25 (s, 2H).
14. (a) Meyers, A. I.; Avila, W. B. Tetrahedron Lett. 1980, 3335; (b) Shimano, M.; Meyers, A. I. Tetrahedron Lett. 1997, 5415.
15. Methyl ester of compound 11: 1H NMR (CDCl3): 2.75 (br s, OH), 3.92 (s, 6H), 5.17 (d, J=10.40 Hz, 1H), 5.30 (d, J=17.18
Hz, 1H), 5.45 (d, J=4.7 Hz, 1H), 6.06 (m, 1H), 7.40 (d, J=7.8 Hz, 1H), 7.55 (s, 1H), 7.64 (d, J=7.8 Hz, 1H).
16. Chong, R.; King, R. R.; Whalley, W. B. J. Chem. Soc. [C] 1971, 3566.
17. (a) Briggs, D. R.; Whalley, W. B. J. Chem. Soc., Perkin Trans. 1 1976, 1382; (b) Manchand, P. S.; Townsend, J. M.; Belica, P.
S.; Wong, H. S. Synthesis 1980, 409; (c) Asahina, Y.; Asano, J. Ber. Dtsch. Chem. Ges. 1933, 66[B], 687; (d) Charlesworth,
E. H.; Robinson, R. J. Chem. Soc. 1934, 1531; (e) Fujikawa, F.; Kobayashi, T. J. Pharm. Soc. Jpn. 1944, 64, 7; (f) Wessely,
F.; Swoboda, J.; Guth, V. Monatsh. Chem. 1964, 95, 649; (g) Tyman, J. H. P. J. Chem. Soc., Perkin Trans. 1 1973, 1639.