Regioselective Synthesis of 3-Alkynyl-5-bromo-2-pyrones via Pd-Catalyzed Couplings on 3,5-Dibromo-2-pyrone

Organic Letters

Volumn 4, Issue 7, 2002, Pages 1171-1173

  Lee, Jin Hee ^a   Park, Jung Sang ^a   Cho, Cheon Gyu ^a  

^a Hanyang University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE;

EID: 0000303942     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025613q     Document Type: Article

References (31)

1. (a) Schlingmann, G.; Milne, L.; Carter, G. T. Tetrahedron 1998, 54, 13013.
2. (b) Shi, X.; Leal, W. S.; Liu, Z.; Schrader, E.; Meinwald, J. Tetrahedron Lett. 1995, 36, 71.
3. (c) Barrero, A. F.; Oltra, J. E.; Herrador, M. M.; Sanchez, J. F.; Quilez, J. F.; Rojas, F. J.; Reyes, J. F. Tetrahedron 1993, 49, 141.
4. For representative examples, see: (a) Okamura, H.; Shimizu, H.; Iwagawa, T.; Nakatani, M. Tetrahedron Lett. 2000, 41, 4147.
5. (b) Posner, G. H.; Lee, J. K.; White, M. W.; Hutchings, R. H.; Dai, H.; Kachinski, J. L.; Dolan, P.; Kensler, T. W. J. Org. Chem. 1997, 62, 3299 and references cited therein.
6. (c) Posner, G. H.; Cho, C.-G.; Anjeh, T. E. N.; Johnson, N.; Horst, R. L.; Kobayashi, T.; Okano, T.; Tsugawa, N. J. Org. Chem. 1995, 60, 4617.
7. (d) Nicolaou, K. C.; Yang, Z.; Liu, J. J.; Ueno, H. et al. Nature, 1994, 367, 630.
8. (a) Afarinkia, K.; Vinader, V.; Nelson, T. D.; Posner, G. H. Tetrahedron 1992, 48, 9111.
9. (b) Kvita, V.; Fischer, W. Chimia 1993, 47, 3.
10. (c) Afarinkia, K.; Berna-Canovas, J. Tetrahedron Lett. 2000, 41, 4955.
11. (d) Okamura, H.; Shimizu, H.; Nakamura, Y.; Iwagawa, T.; Nakatani, M. Tetrahedron Lett. 2000, 41, 4147.
12. (e) Yao, S.; Roberson, M.; Reichel, F.; Hazell, R. G.; Jorgensen, K. A. J. Org. Chem. 1999, 64, 6677.
13. (f) Stigers, K. D.; Mar-Tang, R.; Bartlett, P. A. J. Org. Chem. 1999, 64, 8409.
14. (g) Kotretsou, S. I.; Georgiadis, M. P. Org. Prep. Proced. Int. 2000, 32, 161.
15. (h) Larock, R. C.; Doty, M. J.; Han, X. J. Org. Chem. 1999, 64, 8770.
16. (i) Bodwell, G.; Pi, Z.; Potti, I. R. Synlett 1999, 4, 477.
17. (j) Liebeskind, L. S.; Wang, J. Tetrahedron 1993, 49, 5461.
18. (a) Danieli, B.; Lesma, G.; Martinelli, M.; Passarella, D.; Peretto, I.; Silvani, A. Tetrahedron 1998, 54, 14081.
19. (b) Liu, Z.; Meinwald, J. J. Org. Chem. 1996, 61, 6693.
20. (c) Cerezo, S.; Moreno-Manas, M.; Pleixats, R. Tetrahedron 1998, 54, 7813.
21. (d) Bellina, F.; Biagetti, M.; Carpita, A.; Rossi, R. Tetrahedron Lett. 2001, 42, 2859.
22. (e) Posner, G.; Harrison, W.; Wettlaufer, D. J. Org. Chem. 1985, 50, 5014.
23. Cho, C.-G.; Park, J.-S.; Kim, Y.-W.; Lee, H. Tetrahedron Lett. 2001, 42, 1065.
24. (a) Cho, C.-G.; Kim, Y.-W.; Lim, Y.-K.; Park, J.-S.; Lee, H.; Koo, S. J. Org. Chem. 2002, 67, 290.
25. (b) Cho, C.-G.; Kim, Y.-W.; Kim, W.-K. Tetrahedron Lett. 2001, 42, 8193.
26. (a) Bach, T.; Kruger, L.; Synlett 1998, 1185.
27. (b) Bach, T.; Kruger, L. Tetrahedron Lett. 1998, 39, 1729.
28. (a) Sonogashira, K. In Comprehensive Organic Syntheses; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 3, pp 521-549.
29. (b) Hundertmark, T.; Littke, A. F.; Buchwald, S. L.; Fu, G. C. Org. Lett. 2000, 2, 1729.
30. 2 270.9790, found 270.9789.
31. Babudri, F.; Fiandanese, V.; Marchese, G.; Punzi, A. J. Organomet. Chem. 1998, 566, 251.