W. V. Murray et al. / Tetrahedron Letters 43 (2002) 7389–7392
7391
Figure 1. IMDA products from the triene precursors.
136.6, 152.3, 169.6, 174.1 The LC/MS calculated: 405.2
found (M+H)+=406.2, found (M+Na)+=428.2,
HRFABMS (M+H)+ calculated=405.2011, found
405.2018; [h]2D0 +58 (c 0.10, CHCl3).
Y.; Green, M. A.; Bergstrom, D. E. J. Comb. Chem. 2000,
2, 297 and references 2–9 therein; (d) Polyak, F.; Lubell,
W. D. J. Org. Chem. 2001, 66, 1171; (e) Feng, Z.; Lubell,
W. D. J. Org. Chem. 2001, 66, 1181.
2. For synthesis of other hydroisoquinone and hydroisoin-
dole derivatives via Diels–Alder reactions, see: (a) Guitier-
rez, A. J.; Shea, K. J.; Svoboda, J. J. J. Org. Chem. 1989,
54, 4335; (b) Moriwake, T.; Hmano, S.; Saito, S.; Torii, S.;
J. Org. Chem. 1989, 54, 4114; (c) Martin, S.; Williamson,
S. A.; Gist, R. P.; Smith, K. M. J. Org. Chem. 1983, 48,
5170; (d) Guy, A.; Lemaire, M.; Negre, M.; Guette, J. P.
Tetrahedron Lett. 1985, 26, 3575; (e) Takeuchi, H.; Fuji-
moto, T.; Hshino, K.; Motoyoshia, J.; Kakehi, A.;
Yamamoto, I. J. Org. Chem. 1998, 63, 7172.
3. For synthesis of 6,5 fused systems via oxo Diels–Alder
reactions, see: Tietze, L. F.; Beifuss, U.; Ruthe, M.;
Ruhlmann, A.; Antel, J.; Sheldrick, G. M. Angew. Chem.,
Int. Ed. 1988, 27, 1186–1187; Tietze, L. F.; Bachmann, J.;
Scul, W. Angew. Chem., Int. Ed. 1988. 27, 971–973.
4. (a) Murray, W. V.; Sun, S.; Turchi, I. J.; Brown, F. K.;
Gauthier, A. D. J. Org. Chem. 1999, 64, 5930; (b) Sun, S.;
Turchi, I. J.; Murray, W. V. J. Org. Chem. 2000, 65, 2555;
(c) Sun, S.; Murray, W. V. J. Org. Chem. 1999, 64, 5941.
5. Synthesis of amino aldehydes and their stability, see: (a)
Myers, A. G.; Zhong, B.; Movassaghi, M.; Kung, D. W.;
Lanman, B. A.; Kwon, S. Tetrahedron Lett. 2000, 41,
1359–1362; (b) Myers, A. G.; Kung, D. W.; Zhong, B. J.
Am. Chem. Soc. 2000, 122, 3226. J. Chem. Soc., Chem.
Preparation of 7a: The cycloaddition product 1a (0.11g,
27 mmol) was dissolved in toluene (5 mL) and water
(0.5 mL). The reaction mixture was stirred for 16 h.
The residual toluene/H2O was then removed in vacuo.
After chromatography 7a (0.089 g, 0.21 mmol, 78%)
was isolated by eluting the desired compound with 20%
1
EtOAc/CH2Cl2. H NMR (CDCl3, 300 MHz) l 1.21 (t,
J=7.12, 3H), 1.75–1.85 (m, J=13.70, J=3.31, 1H),
1.98 (s, 3H), 2.30 (m, 1H), 2.55 (dd, J=13.75, J=3.41,
1H), 2.70–2.98 (m, 2H), 3.31 (bs, OH), 3.60 (m, 2H),
3.90 (m, 1H), 4.10 (m, 2H), 4.15 (d, J=14.90, 1H),
5.00–5.10 (d, J=14.90, 1H). 6.85–7.50 (m, 10H). 13C
NMR (CDCl3, 75 MHz) l: 22.7, 29.3, 30.0, 37.5, 38.6,
43.8, 44.8, 59.1, 62.1, 71.1, 126.7, 127.0, 127.5, 127.7,
128.0, 128.5, 128.7, 129.1, 129.9, 135.9, 136.3, 138.6,
173.1, 175.0, 207.3. LC/MS calculated: 423.2, found
423.2, and (M+Na)+=446.2. [h]D20 +78 (c 0.32, CHCl3).
References
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