846
LETTERS
SYNLETT
References
Tohma, H.; Inagaki, M.; Hatanaka, K.; Yakura, T. J. Am. Chem.
Soc. 1992, 114, 2175.
(1) Molinski, T. F. Chem. Rev. 1993, 93, 1825.
(2) Radisky, D. C.; Radisky, E. S.; Barrows, L. R.; Copp, B. R.;
(8) Compound 7 was produced from 4 and succinic anhydride with
continuous removal of water. Piutti, A. Chem. Ber. 1896, 29, 84.
Kramer, R. A.; Ireland, C. M. J. Am. Chem. Soc. 1993, 115, 1632.
(3) Sun, H. H.; Sakemi, S.; Burres, N.; McCarthy, P. J. Org. Chem.
1990, 55, 4964.
(9) Nucleophilic aromatic substitution: Terrier, F. Chem. Rev. 1982,
82, 77.
(4) Venables, D. A.; Barrows, L. R.; Lassota, P.; Ireland, C. M.
(10) A 2D COSY experiment on compound 10 confirmed the
Tetrahedron Lett. 1997, 38, 721.
tetrahydroquinoline structure.
(5) Perry, N. B.; Blunt, J. W.; Munro, M. H. G.; Higa, T.; Sakai, R. J.
Org. Chem. 1988, 53, 4621.
(11) Fewer equivalents produced an inseparable mixture of starting
material, aldehyde and alcohol. The ratio of aldehyde to alcohol
was 4:1.
(6) Copp, B. R.; Ireland, C. M.; Barrows, L. R. J. Org. Chem. 1991,
56, 4596.
(12) Compound 12: 300 MHz NMR (CDCl ) δ 2.94 (t, J=5.7 Hz, 2 H),
3
(7) White, J. D.; Yager, K. M.; Yakura, T. J. Am. Chem. Soc. 1994,
116, 1831. Roberts, D.; Joule, J. A.; Bros, M. A.; Alvarez, M. J.
Org. Chem. 1997, 62, 568. Yamada, F.; Hamabuchi, S.; Shimizu,
A.; Somei, M. Heterocycles 1995, 41, 1905. Peat, A. J.;
Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 1028. Sadanandan,
E. V.; Pillai, S. K.; Lakshmikantham, M. V.; Billimoria, A. D.;
Culpepper, J. S.; Cava, M. P. J. Org. Chem. 1995, 60, 1800. Zhao,
R.; Lown, W. Synth. Comm. 1997, 27, 2103. Makoza, M.;
Stalewski, J.; Maslennikova, O. S. Synthesis 1997, 1131. Kita, Y.;
3.43 (t, J=5.7 Hz, 2 H), 3.84 (s, 3 H), 5.79 (s, 1 H), 6.58 (s, 1 H),
13
7.66 (brs, 1 H). 75 MHz C NMR (CDCl + CD COCD ) δ 23.0,
3
3
3
43.7, 59.8, 92.0, 111.2, 113.2, 113.5, 125.4, 128.1, 135.2, 137.6.
Compound 13: 300 MHz NMR (CDCl ) δ 2.22 (s, 3 H), 2.46 (s, 3
3
H), 2.89-3.00 (m, 2 H), 3.98 (s, 3 H), 4.08-4.20 (m, 2 H), 6.84 (s, 1
H), 7.70 (bs, 1 H), 7.87 (bs, 1 H), 8.21 (bs, 1 H). MS m/z for
C
H N O : 287, 230, 188. HRMS m/z for C H N O : calcd.
15 17 3 3 15 17 3 3
287.1270; found 287.1267. Mp 217 °C with decomp.