TiCl 4-promoted tandem carbonyl or imine addition and friedel-crafts cyclization: Synthesis of benzo-fused oxabicyclooctanes and nonanes

Organic Letters

Volumn 14, Issue 8, 2012, Pages 2002-2005

  Ghosh, Arun K ^a   Martyr, Cuthbert D ^a   Xu, Chun Xiao ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE; CYCLOALKANE DERIVATIVE; FURAN DERIVATIVE; FUSED HETEROCYCLIC RINGS; NONANE; TITANIUM; TITANIUM TETRACHLORIDE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; CYCLIZATION; STEREOISOMERISM; SYNTHESIS;

ALKANES; BICYCLO COMPOUNDS, HETEROCYCLIC; CATALYSIS; COMBINATORIAL CHEMISTRY TECHNIQUES; CYCLIZATION; CYCLOPARAFFINS; FURANS; MOLECULAR STRUCTURE; STEREOISOMERISM; TITANIUM;

EID: 84860121372     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300494q     Document Type: Article

References (27)

1. Ghosh, A. K.; Anderson, D. D.; Weber, I. T.; Mitsuya, H. Angew. Chem., Int. Ed. 2012, 51, 2-27
2. Han, L.; Huang, X.; Sattler, I.; Moellmann, U.; Lin, W.; Grabley, S. Planta Med. 2005, 17, 160-164
3. Lefort, A.; Baptista, M.; Fantin, B.; Depardieu, F.; Arthur, M.; Carbon, C.; Courvalin, P. Antimicrob. Agents Chemother. 1999, 43, 476-482
4. Sammes, P. G.; Whitby, R. J. J. Chem. Soc., Chem. Commun. 1984, 702-703
5. Marson, C. M.; Campbell, J.; Hursthouse, M. B.; Abdul Malic, K. M. Angew. Chem., Int. Ed. 1998, 37, 1122-1124
6. Oda, K.; Nakagami, R.; Nishizono, N.; Machida, M. Chem. Lett. 2000, 29, 1386-1387
7. Wu, Y.; Li, Y.; Wu, Y.-L. Helv. Chim. Acta 2001, 84, 163-171
8. Solorio, D. M.; Jennings, M. P. J. Org. Chem. 2007, 72, 6621-6623
9. Ramana, C. V.; Salian, S. R.; Gonnade, R. G. Eur. J. Org. Chem. 2007, 5483-5486
10. Fananas, F. J.; Fernandez, A.; Cevic, D.; Rodriguez, F. J. Org. Chem. 2009, 74, 932-934
11. Sarkar, D.; Venkateswaran, R. V. Tetrahedron Lett. 2011, 52, 3232-3233
12. Hu, B.; Xing, X.; Ren, J.; Wang, Z. Tetrahedron 2010, 66, 5671-5674
13. Ghosh, A. K; Kawahama, R. Tetrahedron Lett. 1999, 40, 1083-1086
14. Ghosh, A. K; Kawahama, R. Tetrahedron Lett. 1999, 40, 4751-4754
15. Ghosh, A. K; Kawahama, R; Wink, D. Tetrahedron Lett. 2000, 41, 8425-8429
16. Ghosh, A. K; Xu, C.-X; Kulkarni, S. S; Wink, D. Org. Lett. 2005, 7, 7-10
17. Ghosh, A. K; Kulkarni, S; Xu, C-X; Fanwick, P. E. Org. Lett. 2006, 8, 4509-4511
18. Ghosh, A. K; Kass, J. Chem. Commun. 2010, 46, 1218-1220
19. Ghosh, A. K.; Kawahama, R. J. Org. Chem. 2000, 65, 5433-5435
20. Ghosh, A. K.; Kass, J. Org. Lett. 2012, 14, 510-512
21. Ghosh, A. K. PCT Int. appl. 2009, WO 2009091941 A1 20090723.
22. Povarov, L. S.; Mikhailov, B. M. Izv. Akad. Nauk SSR, Ser. Khim. 1963, 953-956
23. Kouznetsov, V. V. Tetrahedron. 2009, 65, 2721-2750
24. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815-3819
25. Walker, J.; Chen, J.; Wise, D. S; Townsend, L. B. J. Org. Chem. 1996, 61, 2219-2221
26. Single-crystal X-ray analysis was performed in-house; Dr. Phil Fanwick, X-ray Crystallography laboratory, Department of Chemistry, Purdue University, West Lafayette, IN 47907.
27. CCDC 867872 contains the supplementary crystallographic data for compound 5b. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.