Divergent Diels-Alder methodology from methyl coumalate toward functionalized aromatics

Tetrahedron Letters

Volumn 54, Issue 19, 2013, Pages 2366-2368

  Lee, Jennifer J ^a   Kraus, George A ^a  

^a IOWA STATE UNIVERSITY   (United States)

Author keywords

Functionalized aromatics; Inverse electron demand Diel Alder; Ketal Orthoester; Methyl coumalate; Vinyl ether

Indexed keywords

AROMATIC COMPOUND;

AROMATIZATION; ARTICLE; CATALYST; DIELS ALDER REACTION; ISOMERIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PURIFICATION; ROOM TEMPERATURE; SYNTHESIS;

ALNUS;

EID: 84875938263     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.02.083     Document Type: Article

References (33)

1. K.C. Nicolaou, S.A. Snyder, T. Montagnon, and G. Vassilikogiannakis Angew. Chem., Int. Ed. 41 2002 1668 1698
2. K. Afarinkia, V. Vinader, R.D. Nelson, and G.H. Posner Tetrahedron 48 1992 9111 9171
3. J.H. Boyer, and W. Schoen Org. Synth. 36 1956 44
4. G.H. Posner, J.-C. Carry, J.K. Lee, D.S. Bull, and H. Dai Tetrahedron Lett. 35 1994 1321 1324
5. I.E. Markó, and G.R. Evans Tetrahedron Lett. 34 1993 7309 7312
6. C.-H. Chen, and C.-C. Liao Org. Lett. 2 2000 2049 2052
7. A.D. Carbaugh, W. Vosburg, T.J. Scherer, C.E. Castillo, M.A. Christianson, J. Kostarellas, S.J. Gosai, and M.S. Leonard ARKIVOC 12 2007 43 54
8. G.A. Kraus, S. Riley, and T. Cordes Green Chem. 13 2011 2734 2736
9. H. Hashizume, H. Ito, N. Kanaya, H. Nagashima, H. Usui, R. Oshima, M. Kanao, H. Tomoda, T. Sunazuka, H. Kumagai, and S. Omura Chem. Pharm. Bull. 42 1994 1272 1278
10. N. Haga, and H. Takayanagi J. Org. Chem. 61 1996 735 745
11. C.-W. Kuo, and J.-M. Fang Synth. Commun. 31 2001 877 892
12. G.A. Kraus, M.E. Krolski, and J. Sy Org. Synth. 67 1989 202 203
13. M. Dong, J. Zhang, X. Peng, H. Lu, L. Yun, S. Jiang, and Q. Dai Eur. J. Med. Chem. 45 2010 4096 4103
14. J. Qiu, B. Xu, Z. Huang, W. Pan, P. Cao, C. Liu, X. Hao, B. Song, and G. Liang Bioorg. Med. Chem. 19 2011 5352 5360
15. F. Effenberger, and R. Ziegler Chem. Ber. 120 1987 1339 1346
16. V. Divya, S. Biju, R.L. Varma, and M.L.P. Reddy J. Mater. Chem. 20 2010 5220 5227
17. Y. Yang, J.O. Escobedo, A. Wong, C.M. Schowalter, M.C. Touchy, L. Jiao, W.E. Crowe, F.R. Fronczek, and R.M. Strongin J. Org. Chem. 70 2005 6907 6912
18. X. Li, A. Bhandari, C.P. Holmes, and A.K. Szardenings Bioorg. Med. Chem. Lett. 14 2004 4301 4306
19. X.-H. Xu, A. Azuma, A. Kusuda, E. Tokunaga, and N. Shibata Eur. J. Org. Chem. 8 2012 1504 1508
20. X. Chen, H. Ke, Y. Chen, C. Guan, and G. Zou J. Org. Chem. 77 2012 7572 7578
21. P. von Zezschwitz, F. Petry, and A. de Meijere Chem. Eur. J. 7 2001 4035 4046
22. R.L. Snowden, and M. Wüst Tetrahedron Lett. 27 1986 703 704
23. T.H. Chan, and C.V.C. Prasad J. Org. Chem. 51 1986 3012 3016
24. N. Atanes, S. Escudero, D. Pérez, E. Guitián, and L. Castedo Tetrahedron Lett. 39 1998 3039 3040
25. A.E. Kümmerle, M. Schmitt, S.V.S. Cardozo, C. Lugnier, P. Villa, A.B. Lopes, N.C. Romeiro, H. Justiniano, M.A. Martins, C.A.M. Fraga, J.-J. Bourguignon, and E.J. Barreiro J. Med Chem. 55 2012 7525 7545
26. Maring, C. J.; Pratt, J. K.; Carroll, W. A.; Liu, D.; Betebenner, D. A.; Hutchinson, D. K.; Tufano, M. D.; Rockway, T. W.; Schoen, U.; Pahl, A.; Witte, A. U.S. Patent 065558, 2011.
27. H. Behringer, and P. Heckmaier Chem. Ber. 102 1969 2835 2850
28. M.E. Jung, and J.A. Hagenah J. Org. Chem. 52 1987 1889 1902
29. G.-S. Koo, E.-H. Kim, and K.-J. Lee Synth. Commun. 32 2002 2275 2286
30. M.I. El-Gamal, and C.-H. Oh Bull. Korean Chem. Soc. 32 2011 821 828
31. R.M. Tynebor, M.-H. Chen, S.R. Natarajan, E.A. O'Neill, J.E. Thompson, C.E. Fitzgerald, S.J. O'Keefe, and J.B. Doherty Bioorg. Med. Chem. Lett. 22 2012 5979 5983
32. D.-J. Chang, E.-Y. Yoon, G.-B. Lee, S.-O. Kim, W.-J. Kim, Y.-M. Kim, J.-W. Jung, H. An, and Y.-G. Suh Bioorg. Med. Chem. Lett. 19 2009 4416 4420
33. Rehwinkel, H.; Baeurle, S.; Berger, M.; Schmees, N.; Schaecke, H.; Krolikiewicz, K.; Mengel, A.; Nguyen, D.; Jaroch, S.; Skuballa, W. U.S. Patent 7,662,821, 2010.