Synthesis of highly oxygenated dinaphthyl ethers via SNAr reactions promoted by Barton's base

Organic Letters

Volumn 5, Issue 7, 2003, Pages 1155-1158

  Wipf, Peter ^a   Lynch, Stephen M ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 TERT BUTYL 1,1,3,3 TETRAMETHYLGUANIDINE; ARGON; ETHER DERIVATIVE; GUANIDINE DERIVATIVE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG; 1 FLUORONAPHTHALENE; 1-FLUORONAPHTHALENE; BUTYL 1,1,3,3 TETRAMETHYLGUANIDINE; BUTYL-1,1,3,3-TETRAMETHYLGUANIDINE; DRUG DERIVATIVE; FUSED HETEROCYCLIC RINGS; GUANIDINE; NAPHTHOL DERIVATIVE; OXYGEN; PALMARUMYCIN CP2; SPIRO COMPOUND;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; ELECTRON; OXYGENATION; SYNTHESIS; CHEMICAL STRUCTURE; CHEMISTRY;

ETHERS; GUANIDINE; HETEROCYCLIC COMPOUNDS WITH 4 OR MORE RINGS; MOLECULAR STRUCTURE; NAPHTHALENES; NAPHTHOLS; OXYGEN; SPIRO COMPOUNDS;

EID: 0041728879     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034286z     Document Type: Article

References (34)

1. For examples of biologically active natural products containing diaryl ethers, see: (a) Rama Rao, A. V.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev. 1995, 95, 2135. (b) Nicolaou, K. C.; Boddy, C. N. C.; Brase, S.; Winssinger, N. Angew. Chem., Int. Ed. Engl. 1999, 38, 2097. (c) Yasuzawa, T.; Shirahata, K.; Sano, H. J. Antibiot. 1987, 40, 455. (d) Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909.
2. For examples of biologically active natural products containing diaryl ethers, see: (a) Rama Rao, A. V.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev. 1995, 95, 2135. (b) Nicolaou, K. C.; Boddy, C. N. C.; Brase, S.; Winssinger, N. Angew. Chem., Int. Ed. Engl. 1999, 38, 2097. (c) Yasuzawa, T.; Shirahata, K.; Sano, H. J. Antibiot. 1987, 40, 455. (d) Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909.
3. For examples of biologically active natural products containing diaryl ethers, see: (a) Rama Rao, A. V.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev. 1995, 95, 2135. (b) Nicolaou, K. C.; Boddy, C. N. C.; Brase, S.; Winssinger, N. Angew. Chem., Int. Ed. Engl. 1999, 38, 2097. (c) Yasuzawa, T.; Shirahata, K.; Sano, H. J. Antibiot. 1987, 40, 455. (d) Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909.
4. For examples of biologically active natural products containing diaryl ethers, see: (a) Rama Rao, A. V.; Gurjar, M. K.; Reddy, K. L.; Rao, A. S. Chem. Rev. 1995, 95, 2135. (b) Nicolaou, K. C.; Boddy, C. N. C.; Brase, S.; Winssinger, N. Angew. Chem., Int. Ed. Engl. 1999, 38, 2097. (c) Yasuzawa, T.; Shirahata, K.; Sano, H. J. Antibiot. 1987, 40, 455. (d) Jung, M. E.; Rohloff, J. C. J. Org. Chem. 1985, 50, 4909.
5. (a) Lindley, J. Tetrahedron 1984, 40, 1433.
6. (b) Theil, F. Angew. Chem., Int. Ed. 1999, 38, 2345.
7. (c) Buck, E.; Song, Z. J.; Tschaen, D.; Dormer, P. G.; Volante, R. P.; Reider, P. J. Org. Lett. 2002, 4, 1623.
8. (a) Wipf, P.; Jung, J.-K.; Rodriguez, S.; Lazo, J. S. Tetrahedron 2001, 57, 283.
9. (b) Wipf, P.; Hopkins, T. D.; Jung, J.-K.; Rodriguez, S.; Birmingham, A. ; Southwick, E. C.; Lazo, J. S.; Powis, G. Bioorg. Med. Chem. Lett. 2001, 11, 2637.
10. (a) Wipf, P.; Jung, J.-K. J. Org. Chem. 2000, 65, 6319.
11. (b) Wipf, P.; Jung, J.-K. J. Org. Chem. 1999, 64, 1092.
12. (a) McDonald, L. A.; Abbanat, D. R.; Barbieri, L. R.; Bernan, V. S.; Discafani, C. M.; Greenstein, M.; Janota, K.; Korshalla, J. D.; Lassota, P.; Tischler, M.; Carter, G. T. Tetrahedron Lett. 1999, 40, 2489.
13. (b) Wang, T.; Shirota, O.; Nakanishi, K.; Berova, N.; McDonald, L. A.; Barbieri, L. R.; Carter, G. T. Can. J. Chem. 2001, 79, 1786.
14. For a recent review, see: Sawyer, J. S. Tetrahedron 2000, 56, 5045.
15. (a) Perez-Gonzalez, M.; Jackson, R. F. Chem. Commun. 2000, 2423.
16. (b) Sawyer, J. S.; Schmittling, E. A.; Palkowitz, J. A.; Smith, W. J., III. J. Org. Chem. 1998, 63, 6338.
17. (c) Keseru, G. M.; Dienes, Z.; Nogradi, M.; Kajtar-Peredy, M. J. Org. Chem. 1993, 58, 6725.
18. (a) Boger, D. L.; Miyazaki, S.; Kim, S. H.; Wu, J. H.; Castle, S. L.; Loiseleur, O.; Jin, Q. J. Am. Chem. Soc. 1999, 121, 10004.
19. (b) Evans, D. A.; Wood, M. R.; Trotter, B. W.; Richardson, T. I.; Barrow, J. C.; Katz, J. L. Angew. Chem., Int. Ed. 1998, 37, 2700.
20. (c) Janetka, J. W.; Rich, D. H. J. Am. Chem. Soc. 1997, 119, 6488.
21. (d) Zhu, J. Synlett 1997, 133.
22. (a) Barton, D. H. R.; Elliott, J. D.; Gero, S. D. J. Chem. Soc., Perkin Trans. 1 1982, 2085.
23. (b) Barton, D. H. R.; Charpiot, B.; Motherwell, W. B. Tetrahedron Lett. 1982, 3365.
24. (a) Barrett, A. G. M.; Cramp, S. M.; Roberts, R. S.; Zecri, F. J. Org. Lett. 1999, 1, 579.
25. (b) Barrett, A. G. M.; Cramp, S. M.; Hennessy, A. J.; Procopiou, P. A.; Roberts, R. S. Org. Lett. 2001, 3, 271.
26. Barton's base is commercially available from Fluka or may be prepared: Barton, D. H. R.; Chen, M.; Jaszberenyi, J. C.; Taylor, D. K. Org. Synth. 1996, 74, 101.
27. 4), and concentrated under reduced pressure. Trituration of the residue with cold hexanes/EtOAc (4:1) afforded 275 mg (84%) of 15 as a beige solid: mp 132-133°C (EtOAc/hexanes).
28. Krow, G. R. Org. React. 1993, 43, 251.
29. (a) Wipf, P.; Jung, J.-K. Angew. Chem., Int. Ed. Engl. 1997, 36, 764.
30. (b) Boswell, G. E.; Licause, J. F. J. Org. Chem. 1995, 60, 6592.
31. (c) Yeager, G. W.; Schissel, D. N. Synthesis 1991, 63.
32. (a) Akai, S.; Kita, Y. Org. Prep. Proc. Int. 1998, 30, 603.
33. (b) Coutts, I. G. C.; Allcock, R. W.; Scheeren, H. W. Tetrahedron Lett. 2000, 41, 9105.
34. (c) Pelter, A.; Elgendy, S. Tetrahedron Lett. 1988, 29, 677.