Base-induced rearrangement of bicyclo[3.3.1]nonan-3-ones to polysubstituted hexahydronaphthalenes

Synlett

Volumn , Issue 5, 2001, Pages 664-666

  Geirsson, Jon K F ^a   Eiriksdottir, Emelia G ^a  

^a UNIVERSITY OF ICELAND   (Iceland)

Author keywords

1 Tetralones; Bicyclo 3.3.1 nonan 3 ones; Hexahydronaphthalenes; Resorcinols

Indexed keywords

1 TETRALONE DERIVATIVE; ACETONE; BICYCLO[3.3.1]NONANE DERIVATIVE; NAPHTHALENE DERIVATIVE; RESORCINOL DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CRYSTAL STRUCTURE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0035026306     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2001-13373     Document Type: Article

References (20)

1. Geirsson, J. K. F.; Johannesdottir, J. F. J. Org. Chem. 1996, 61, 7320.
2. Tested for us by Dr. V. L. Narayanan and his team at the National Cancer Institute, Bethesda, MD.
3. Neh, H.; Blechert, S.; Schnick, W.; Jansen, M. Angew. Chem. 1984, 96, 903. Blechert, S.; Kleine-Klausing, A. Angew. Chem., Int. Ed. Engl. 1991, 30, 412.
4. Neh, H.; Blechert, S.; Schnick, W.; Jansen, M. Angew. Chem. 1984, 96, 903. Blechert, S.; Kleine-Klausing, A. Angew. Chem., Int. Ed. Engl. 1991, 30, 412.
5. Blechert, S.; Jansen, R.; Velder, J. Tetrahedron 1994, 50, 9649.
6. Rodriguez, J. Synlett 1999, 505. Rainier, J. D.; Xu, Q. Org. Lett. 1999, 1, 1161.
7. Rodriguez, J. Synlett 1999, 505. Rainier, J. D.; Xu, Q. Org. Lett. 1999, 1, 1161.
8. Lavoisier-Gallo, T.; Charonnet, E; Rodriguez, J. J. Org. Chem. 1998, 63, 900.
9. 9: C, 55.43; H, 5.47; O, 39.09. Found: C, 55.38; H, 5.52.
10. Williams, D, H.; Fleming, I. Spectroscopic Methods in Organic Chemistry; 5th ed.; McGraw-Hill: London, 1995, pp 99-100.
11. Crystallographic data for 2a has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC 156072. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1E2, UK, (fax:+44 1223 336033 or e-mail: deposit@ccdc.cam.ac.uk).
12. Geirsson, J. K. F.; Johannesdottir, J. F.; Jonsdottir, S. Synlett 1993, 133. Geirsson, J. K. F. In Recent Research Developments in Organic Synthesis; Pandalai, S. G., Ed.; Transworld Research Network: India, 1998; Vol. 2, 609.
13. Geirsson, J. K. F.; Johannesdottir, J. F.; Jonsdottir, S. Synlett 1993, 133. Geirsson, J. K. F. In Recent Research Developments in Organic Synthesis; Pandalai, S. G., Ed.; Transworld Research Network: India, 1998; Vol. 2, 609.
14. Aoyagi, K.; Nakamura, H.; Yamamoto, Y. J. Org. Chem. 1999, 64, 4148.
15. van Laak, K.; Scharf, H.-D. Tetrahedron 1989, 45, 5511. Hu, Y.-Z.; Clive, D. L. J. J. Chem. Soc., Perkin Trans. I 1997, 1421. Covarrubias-Zuñiga, A.; González-Lucas, A. Tetrahedron Lett. 1998, 39, 2881. Covarrubias-Zúñiga, A.; Maldonado, L. A.; Ríos-Barros, E.; González-Lucas, A. Synth. Commun. 1998, 28, 3461.
16. van Laak, K.; Scharf, H.-D. Tetrahedron 1989, 45, 5511. Hu, Y.-Z.; Clive, D. L. J. J. Chem. Soc., Perkin Trans. I 1997, 1421. Covarrubias-Zuñiga, A.; González-Lucas, A. Tetrahedron Lett. 1998, 39, 2881. Covarrubias-Zúñiga, A.; Maldonado, L. A.; Ríos-Barros, E.; González-Lucas, A. Synth. Commun. 1998, 28, 3461.
17. van Laak, K.; Scharf, H.-D. Tetrahedron 1989, 45, 5511. Hu, Y.-Z.; Clive, D. L. J. J. Chem. Soc., Perkin Trans. I 1997, 1421. Covarrubias-Zuñiga, A.; González-Lucas, A. Tetrahedron Lett. 1998, 39, 2881. Covarrubias-Zúñiga, A.; Maldonado, L. A.; Ríos-Barros, E.; González-Lucas, A. Synth. Commun. 1998, 28, 3461.
18. van Laak, K.; Scharf, H.-D. Tetrahedron 1989, 45, 5511. Hu, Y.-Z.; Clive, D. L. J. J. Chem. Soc., Perkin Trans. I 1997, 1421. Covarrubias-Zuñiga, A.; González-Lucas, A. Tetrahedron Lett. 1998, 39, 2881. Covarrubias-Zúñiga, A.; Maldonado, L. A.; Ríos-Barros, E.; González-Lucas, A. Synth. Commun. 1998, 28, 3461.
19. Watanabe, T.; Oku, Y.; tshii, H.; Ishikawa, T. Synlett 1997, 161. Shin, H.; Deng, L.; Carrera, C. J.; Adachi, S.; Cottam, H. B.; Carson, S. A. Bioorg. Med. Chem. Lett. 2000, 10, 487.
20. Watanabe, T.; Oku, Y.; tshii, H.; Ishikawa, T. Synlett 1997, 161. Shin, H.; Deng, L.; Carrera, C. J.; Adachi, S.; Cottam, H. B.; Carson, S. A. Bioorg. Med. Chem. Lett. 2000, 10, 487.