4120
Scheme 3.
References
1. Harvey, R. G. Polycyclic Aromatic Hydrocarbons: Chemistry and Carcinogenecity; Cambridge University Press:
Cambridge, England, 1991.
2. (a) Manning, W. B.; Tomaszewski, J. E.; Muschik, G. M.; Sato, R. I. J. Org. Chem. 1977, 42, 3465–3468. (b) Muschik, G.
M.; Tomaszewski, J. E.; Sato, R. I.; Manning, W. B. J. Org. Chem. 1979, 44, 2150–2153. (c) Kelly, T. R.; Magee, J. A.;
Weibel, F. R. J. Am. Chem. Soc. 1980, 102, 798–799. (d) Manning, W. B.; Wilbur, D. J. J. Org. Chem. 1980, 45, 733–734.
(e) Kita, Y.; Yasuda, H.; Tamura, O.; Tamura, Y. Tetrahedron Lett. 1984, 25, 1813–1816.
3. (a) Rosen, B. I.; Weber, W. P. J. Org. Chem. 1977, 42, 3463–3465. (b) Manning, W. B.; Kelly, T. P.; Muschik, G. M. J.
Org. Chem. 1980, 45, 2535–2536. (c) Willmore, N. D.; Hoic, D. A.; Katz, T. J. J. Org. Chem. 1994, 59, 1889–1891. (d)
Zhang, Z.; Flachsmann, F.; Moghaddam, F. M.; Rüedi, P. Tetrahedron Lett. 1994, 35, 2153–2156. For other synthesis of
1,4-phenanthrenquinones, see: (e) Mallory, F. B.; Mallory, C. W. In Organic Reactions, Vol. 30; Daulen, W. G., Ed.; Wiley:
New York, 1984. (f) Kraus, G. A.; Melekhov, A. J. Org. Chem. 1999, 64, 1720–1722.
4. (a) Nuckolls, C.; Katz, T. J.; Castellanos, L. J. Am. Chem. Soc. 1996, 118, 3767–3768. (b) Carreño, M. C.; Hérnandez-
Sánchez, R.; Mahugo, J.; Urbano, A. J. Org. Chem. 1999, 64, 1387–1390.
5. (a) Schmale, H. W.; Jarchow, O. H.; Hausen, B. M.; Werdin, R.; Schulz, K. H.; Krohn, K.; Loock, U. Acta Crystallogr. Sect
A 1984, 40, C63–C64. (b) Kraus, G. A.; Melekhov, A.; Carpenter, S.; Wannemuhler, Y.; Petrich, J. Bioorg. Med. Chem.
Lett. 2000, 10, 9–11.
6. For an overview, see: (a) Carreño, M. C. Chem. Rev. 1995, 95, 1717–1760. (b) García Ruano, J. L.; Carretero, J. C.; Carreño,
M. C.; Martín Cabrejas, L. M.; Urbano, A. Pure Appl. Chem. 1996, 68, 925–930.
7. (a) Carreño, M. C.; García Ruano, J. L.; Urbano, A. Tetrahedron Lett. 1989, 30, 4003–4006. (b) Carreño, M. C.; García
Ruano, J. L.; Toledo, M. A.; Urbano, A.; Remor, C. Z.; Stefani, V.; Fischer, J. J. Org. Chem. 1996, 61, 503–509. (c) Carreño,
M. C.; García Ruano, J. L.; Urbano, A.; Remor, C. Z.; Arroyo, Y. J. Org. Chem. 2000, 65, 453–458.
8. (a) Carreño, M. C.; Urbano, A.; Fischer, J. Angew. Chem., Int. Ed. Engl. 1997, 36, 1621–1623. (b) Carreño, M. C.; García
Ruano, J. L.; Remor, C. Z.; Urbano, A.; Fischer, J. Tetrahedron Lett. 1997, 38, 9077–9080. (c) Carreño, M. C.; Urbano,
A.; Di Vitta, C. J. Org. Chem. 1998, 63, 8320–8330. (d) Carreño, M. C.; García-Cerrada, S.; Urbano, A.; Di Vitta, C.
Tetrahedron: Asymmetry 1998, 9, 2965–2969. (e) Carreño, M. C.; Urbano, A.; Di Vitta, C. Chem. Commun. 1999, 817–818.
(f) Carreño, M. C.; Urbano, A.; Di Vitta, C. Chem. Eur. J. 2000, 6, 906–913.
9. Carreño, M. C.; Mahugo, J.; Urbano, A. Tetrahedron Lett. 1997, 38, 3047–3050.
10. Carreño, M. C.; García Ruano, J. L.; Urbano, A. Synthesis 1992, 651–653.
11. Mixtures of regioisomers were obtained in Diels–Alder reactions of substituted naphthoquinones and styrenes, see: (a)
Manning, W. B. Tetrahedron Lett. 1979, 1661–1664. (b) Manning, W. B. Tetrahedron Lett. 1981, 22, 1571–1574.
1
12. All new compounds were characterized on the basis of their IR, H NMR (300 MHz, CDCl3) and 13C NMR (75 MHz,
CDCl3) spectral data, elemental analysis and/or HRMS.
13. Cycloadditions of sulfinylnaphthoquinones and 1-methoxy-1,3-cyclohexadiene yielded regioselectively the ortho adduct,
see: Carreño, M. C.; García Ruano, J. L.; Urbano, A. J. Org. Chem. 1992, 57, 6870–6876.
14. Wunderly, S. W.; Weber, W. P. J. Org. Chem. 1978, 43, 2277–2279.
15. In the 1H NMR spectrum of 9b H1 appeared shielded (δ=9.02 ppm) if compared with the same proton in 8b (δ=9.20 ppm)
probably due to the loss of planarity of the carbonyl group at C-12 as a consequence of the closeness with the methoxy