Synthesis of functionalized naphthalenes from substituted 1-methoxybenzocyclobutenes

Journal of Organic Chemistry

Volumn 61, Issue 8, 1996, Pages 2885-2887

  Andersen, Neil G ^a   Maddaford, Shawn P ^a   Keay, Brian A ^a  

^a UNIVERSITY OF CALGARY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001115514     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo951978v     Document Type: Article

References (24)

1. Loudon, G. M. Organic Chemistry. 3rd ed.; Benjamin/Cummings Publishing Co., Inc.: Redwood City, CA, 1995; pp 1173-1177.
2. March, J. Advanced Organic Chemistry, 3rd ed.; John Wiley and Sons: New York, 1985; pp 460-461 and references therein.
3. Griffin, R. W., Jr.; Gass, J. D.; Berwick, M. A.; Shulman, R. S. J. Org. Chem. 1964, 29, 2109. Nishino, H.; Kajikawa, S.; Hamada, Y.; Kurosawa, K. Tetrahedron Lett. 1995, 36, 5753. Shishido, K.; Yamahshita, A.; Hiroya, K.; Fukumoto Tetrahedron Lett. 1989, 30, 111.
4. Griffin, R. W., Jr.; Gass, J. D.; Berwick, M. A.; Shulman, R. S. J. Org. Chem. 1964, 29, 2109. Nishino, H.; Kajikawa, S.; Hamada, Y.; Kurosawa, K. Tetrahedron Lett. 1995, 36, 5753. Shishido, K.; Yamahshita, A.; Hiroya, K.; Fukumoto Tetrahedron Lett. 1989, 30, 111.
5. Griffin, R. W., Jr.; Gass, J. D.; Berwick, M. A.; Shulman, R. S. J. Org. Chem. 1964, 29, 2109. Nishino, H.; Kajikawa, S.; Hamada, Y.; Kurosawa, K. Tetrahedron Lett. 1995, 36, 5753. Shishido, K.; Yamahshita, A.; Hiroya, K.; Fukumoto Tetrahedron Lett. 1989, 30, 111.
6. Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 223. Ward, R. S. Nat. Prod. Rep. 1995, 12, 183. Ward, R. S. Nat. Prod. Rep. 1993, 10, 1.
7. Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 223. Ward, R. S. Nat. Prod. Rep. 1995, 12, 183. Ward, R. S. Nat. Prod. Rep. 1993, 10, 1.
8. Faulkner, D. J. Nat. Prod. Rep. 1995, 12, 223. Ward, R. S. Nat. Prod. Rep. 1995, 12, 183. Ward, R. S. Nat. Prod. Rep. 1993, 10, 1.
9. Cristofoli, W.; Keay, B. A. Synlett 1994, 625.
10. Isolation: Roll, D. M.; Scheuer, P. J.; Matsumotao, G. K.; Clardy, J. J. Am Chem. Soc. 1983, 105, 6177 Synthesis: Harada, N.; Sugioka, T.; Ando, Y.; Uda, H.; Kuriki, T. J. Am. Chem. Soc. 1988, 110, 8483.
11. Isolation: Roll, D. M.; Scheuer, P. J.; Matsumotao, G. K.; Clardy, J. J. Am Chem. Soc. 1983, 105, 6177 Synthesis: Harada, N.; Sugioka, T.; Ando, Y.; Uda, H.; Kuriki, T. J. Am. Chem. Soc. 1988, 110, 8483.
12. Isolation: Nakamura, H.; Kobayashi, J.; Kobayashi, M.; Ohizumi, Y.; Hirata, Y. Chem. Lett. 1985, 713. Synthesis: Harada, N.; Sugioka, T.; Uda, H.; Kuriki, T. J. Org. Chem. 1990, 55, 3158. Formal synthesis: Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761.
13. Isolation: Nakamura, H.; Kobayashi, J.; Kobayashi, M.; Ohizumi, Y.; Hirata, Y. Chem. Lett. 1985, 713. Synthesis: Harada, N.; Sugioka, T.; Uda, H.; Kuriki, T. J. Org. Chem. 1990, 55, 3158. Formal synthesis: Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761.
14. Isolation: Nakamura, H.; Kobayashi, J.; Kobayashi, M.; Ohizumi, Y.; Hirata, Y. Chem. Lett. 1985, 713. Synthesis: Harada, N.; Sugioka, T.; Uda, H.; Kuriki, T. J. Org. Chem. 1990, 55, 3158. Formal synthesis: Kanematsu, K.; Soejima, S.; Wang, G. Tetrahedron Lett. 1991, 32, 4761.
15. Charlton, J. L.; Alauddin, M. M. Tetrahedron 1987, 43, 2873.
16. Azadi-Ardakani, M.; Wallace, T. W. Tetrahedron 1988, 44, 5939.
17. Commercon, A.; Normant, J F.; Villieras, J. Tetrahedron 1980, 36, 1215.
18. Azadi-Ardakani, M.; Hayes, R.; Wallace, T. W. Tetrahedron 1990, 46, 6851.
19. Although 1-methoxybenzocyclobutene has been reported to undergo the [4 - 2] cycloaddition reaction via the o-quinodimethane with olefins, we were surprised to find that substituted 1-methoxybenzocyclobutenes have not been used as Diels-Alder precursors, see: (a) Arnold, B. J.; Sammes, P. G.; Wallace, T. W. J. Chem. Soc., Perkin Trans. 1 1974, 409. (b) Moss, R. J.; Rickborn, B. J. Org. Chem. 1984, 49, 3694. (c) Takahashi, Y.; Kochi, J. K. Chem. Ber. 1988, 121, 253. (d) Zhang, X.; Foote, C. S. J. Org. Chem, 1994, 55, 5235.
20. Although 1-methoxybenzocyclobutene has been reported to undergo the [4 - 2] cycloaddition reaction via the o-quinodimethane with olefins, we were surprised to find that substituted 1-methoxybenzocyclobutenes have not been used as Diels-Alder precursors, see: (a) Arnold, B. J.; Sammes, P. G.; Wallace, T. W. J. Chem. Soc., Perkin Trans. 1 1974, 409. (b) Moss, R. J.; Rickborn, B. J. Org. Chem. 1984, 49, 3694. (c) Takahashi, Y.; Kochi, J. K. Chem. Ber. 1988, 121, 253. (d) Zhang, X.; Foote, C. S. J. Org. Chem, 1994, 55, 5235.
21. Although 1-methoxybenzocyclobutene has been reported to undergo the [4 - 2] cycloaddition reaction via the o-quinodimethane with olefins, we were surprised to find that substituted 1-methoxybenzocyclobutenes have not been used as Diels-Alder precursors, see: (a) Arnold, B. J.; Sammes, P. G.; Wallace, T. W. J. Chem. Soc., Perkin Trans. 1 1974, 409. (b) Moss, R. J.; Rickborn, B. J. Org. Chem. 1984, 49, 3694. (c) Takahashi, Y.; Kochi, J. K. Chem. Ber. 1988, 121, 253. (d) Zhang, X.; Foote, C. S. J. Org. Chem, 1994, 55, 5235.
22. Although 1-methoxybenzocyclobutene has been reported to undergo the [4 - 2] cycloaddition reaction via the o-quinodimethane with olefins, we were surprised to find that substituted 1-methoxybenzocyclobutenes have not been used as Diels-Alder precursors, see: (a) Arnold, B. J.; Sammes, P. G.; Wallace, T. W. J. Chem. Soc., Perkin Trans. 1 1974, 409. (b) Moss, R. J.; Rickborn, B. J. Org. Chem. 1984, 49, 3694. (c) Takahashi, Y.; Kochi, J. K. Chem. Ber. 1988, 121, 253. (d) Zhang, X.; Foote, C. S. J. Org. Chem, 1994, 55, 5235.
23. 11
24. Straus, F.; Kollek, L.; Heyn W. Ber. 1930, 63, 1868.