A facile synthesis of homotriptycenes from anthranol derivatives

Synlett

Volumn , Issue 20, 2005, Pages 3166-3168

  Cao, Derong ^a,b   Gao, Chunmei ^a,c   Meier, Herbert ^d  

^a GUANGZHOU INSTITUTE OF CHEMISTRY   (China)

^b SOUTH CHINA UNIVERSITY OF TECHNOLOGY   (China)

^c UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^d JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

Aromatization; Condensation; Electrophilic substitution; Transannular ring closure

Indexed keywords

10 BENZYL 9 ANTHRANOL DERIVATIVE; 10,10 DIBENZYL 9 ANTHRANOL DERIVATIVE; ACID; ANTHRACENE DERIVATIVE; ANTHRANOL DERIVATIVE; HOMOTRIPTYCENE; TRIPTYCENE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; ELECTRON TRANSPORT; POLYMERIZATION; REACTION ANALYSIS; RING CLOSING METATHESIS; SYNTHESIS;

EID: 29744441913     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2005-921929     Document Type: Article

References (26)

1. (a) Kottas, G. S.; Clarke, L. I.; Horinek, D.; Michl, J. Chem. Rev. 2005, 105, 128.
2. (b) Gung, B. W.; Xue, X.; Reich, H. J. J. Org. Chem. 2005, 70, 3641.
3. (c) Godinez, C. E.; Zepeda, G.; Mortko, C. J.; Dang, H.; Garcia-Garibay, M. A. J. Org. Chem. 2004, 69, 1652.
4. (d) Long, T. M.; Swager, T. M. J. Am. Chem. Soc. 2003, 125, 14113.
5. (e) Wiehe, A.; Senge, M.; Schäfer, O. A.; Speck, M.; Tannert, S.; Kurreck, H.; Röder, B. Tetrahedron 2001, 57, 10089.
6. (a) Satrijo, A.; Swager, T. M. Macromolecules 2005, 38, 4054.
7. (b) Perepichka, D. F.; Bendikov, M.; Meng, H.; Wudl, F. J. Am. Chem. Soc. 2003, 125, 10190.
8. Beyeler, A.; Belser, P. Coord. Chem. Rev. 2002, 230, 28.
9. (d) Korth, O.; Wiehe, A.; Kurreck, H.; Röder, B. Chem. Phys. 1999, 246, 363.
10. (e) Norvez, S.; Barzoukas, M. Chem. Phys. Lett. 1990, 16, 41.
11. (a) Xanthopoulou, N. J.; Kourounakis, A. P.; Spyroudis, S.; Kourounakis, P. N. Eur. J. Med. Chem. 2003, 621.
12. (b) Perchellet, E. M.; Sperfslage, B. J.; Wang, Y.; Huang, X.; Tamura, M.; Hua, D. H.; Perchellet, J. P. Anti-Cancer Drugs 2002, 13, 567.
13. (c) Yang, W.; Perchellet, E. M.; Tamura, M.; Hua, D. H.; Perchellet, J. P. Cancer Lett. 2002, 18, 73.
14. (a) Kinbara, K.; Aida, T. Chem. Rev. 2005, 105, 1377.
15. (b) Wolpaw, A. J.; Aizer, A. A.; Zimmt, M. B. Tetrahedron Lett. 2003, 44, 7613.
16. (c) Zhu, Z.; Swager, T. M. J. Am. Chem. Soc. 2002, 124, 9670.
17. (d) Hashimoto, M.; Yamamura, K.; Yamane, J. Tetrahedron 2001, 57, 10253.
18. (e) Müller, T.; Hulliger, J.; Seichter, W.; Weber, E.; Weber, T.; Wübbenhorst, M. Acc. Chem. Res. 2001, 34, 514.
19. Cristol, S. J.; Pennelle, D. X. J. Org. Chem. 1970, 35, 2357.
20. Baumgart, K. D.; Harnish, H.; Seebach, U. S.; Szeimies, G. Chem. Ber. 1985, 110, 2883.
21. Saito, K.; Ito, K.; Takahashi, K.; Kagabu, S. Org. Prep. Proced. Int. 1991, 23, 196.
22. See: (a) Prinz, H.; Ishii, Y.; Hirano, T.; Stoiber, T.; Gomez, J. A. C.; Schmidt, P.; Duessmann, H.; Burger, A. M.; Prehn, J. H. M.; Guenther, E. G.; Unger, E.; Umezawa, K. J. Med. Chem. 2003, 46, 3382.
23. (b) Hu, W. X.; Zhu, W. Bioorg. Med. Chem. Lett. 2004, 14, 621.
24. 2 (328.4): C, 84.12; H, 6.14. Found: C, 84.15; H, 6.17. Structure of 9a could be additionally established by a crystal structure analysis, which shall be published later.
25. (a) Landucci, L. L.; Ralph, J. J. Org. Chem. 1982, 47, 3486.
26. (b) Ralph, J.; Landucci, L. L. J. Org. Chem. 1983, 48, 372.