Tandem Diels-Alder cycloadditions of 2-pyrone-5-acrylates for the efficient synthesis of novel tetracyclolactones

Journal of Organic Chemistry

Volumn 71, Issue 17, 2006, Pages 6701-6704

  Chung, Soo Im ^a   Seo, Joobeom ^b   Cho, Cheon Gyu ^a  

^a Hanyang University   (South Korea)

^b Gyeongsang National University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CARBOXYLIC ACIDS; CATALYSIS; ETHERS; PALLADIUM; SYNTHESIS (CHEMICAL);

ALLYL VINYL ETHERS; COUPLING REACTIONS; DIELS-ALDER CYCLOADDITIONS; TANDEM DIELS-ALDER; TETRACYCLOLACTONES;

ESTERS;

2 PYRONE 5 ACRYLATE DERIVATIVE; 3 BROMO 2 PYRONE 5 CARBOXYLATE; 3,5 DIBROMO 2 PYRONE 5 CARBOXYLATE; ACRYLIC ACID DERIVATIVE; ETHER DERIVATIVE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG; VINYL ETHER DERIVATIVE;

ARTICLE; CATALYSIS; CYCLOADDITION; DIELS ALDER REACTION; OZONOLYSIS; REACTION ANALYSIS; REDUCTION; SYNTHESIS;

EID: 33747432892     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061119e     Document Type: Article

References (30)

1. (a) Winkler, J. D. Chem. Rev. 1996, 96, 167.
2. (b) Ho, T.-L. Tandem Reactions in Organic Synthesis; Wiley: New York, 1992.
3. Winkler, J.; Kim, H.; Kim, S. Tetrahedron Lett. 1995, 687.
4. (a) Wilkie, G. D.; Elliott, G. I.; Blagg, B. S. J.; Wolkenberg, S. E.; Soenen, D. R.; Miller, M. M.; Pollack, S.; Boger, D. L. J. Am. Chem. Soc. 2002, 124, 11292.
5. (b) Wolkenberg, S. E.; Boger, D. L. J. Org. Chem. 2002, 67, 7361.
6. Roush, W. R.; Sciotti, R. J. J. Am. Chem. Soc. 1998, 120, 7411.
7. Vosburg, D. A.; Vanderwal, C. D.; Sorensen, E. J. J. Am. Chem. Soc. 2002, 124, 4552.
8. Heathcock, C.; Hansen, M.; Ruggeri, R.; Kath, J. J. Org. Chem. 1992, 57, 2544.
9. Erase, S.; Wertal, H.; Frank, D.; Vidoviæ, de Meijere, A. Eur. J. Org. Chem. 2005, 4167.
10. (a) Imagawa, T.; Kawanisi, M.; Sisido, K. J. Chem. Soc., Chem. Commun. 1971, 1292.
11. (b) Krantz, A.; Lin, C. J. Am. Chem. Soc. 1973, 95, 5662.
12. (c) Kohnke, F.; Stoddart, J. Pure Appl. Chem. 1989, 61, 1581.
13. (d) Golobish, T. D.; Burke, J. K.; Kim, A. H.; Chong, S. W.; Probst, E. L.; Carroll, P.; Dailey, W. P. Tetrahedron 1998, 54, 7013.
14. (e) Sander, M.; Dehmlow, E. V. Eur. J. Org. Chem. 2001, 399.
15. (f) Afarinkia, K.; Bearpark, M. J.; Ndibwami, A. J. Org. Chem. 2005, 70, 1122.
16. Pang, S.-J.; Min, S.-H.; Lee, H.; Cho, C.-G. J. Org. Chem. 2003, 68, 10191.
17. (a) Ang, C. Y. W.; Hu, L.; Heinze, T. M.; Cui, Y.; Freeman, J. P.; Kozak, K.; Luo, W. J. Agric. Food Chem. 2004, 52, 6156.
18. (b) Kraus, G. A.; Nguyen, T. H.; Jeon, I. Tetrahedron Lett. 2003, 44, 659.
19. (c) Usuda, H.; Kanai, M.; Shibasaki, M. Org. Lett. 2002, 4, 859.
20. (d) Spessard, S. J.; Stoltz, B. M. Org. Lett. 2002, 4, 1943.
21. (e) Young, D. G. J.; Zeng, D. J. Org. Chem. 2002, 67, 3134.
22. (f) Grossman, R. B.; Jacobs, H. Tetrahedron Lett. 2000, 41, 5165.
23. (g) Nicolaou, K. C.; Pfefferkorn, J. A.; Kim, S.; Wei, H. X. J. Am. Chem. Soc. 1999, 121, 4724.
24. (a) Ryu, K.-M; Gupta, A.; Han, J.-W.; Oh, C. H.; Cho, C.-G. Synlett 2004, 2197.
25. (b) Kim, W.-S.; Kim, H.-J.; Cho, C.-G. J. Am. Chem. Soc. 2003, 125, 14288.
26. (l2) All allyl vinyl ethers not commercially available were prepared according to the literature procedures, (a) For entry 1: Watanabe, W. H.; Conlon, L. E. J. Am. Chem. Soc. 1957, 79, 2828.
27. (b) For entry 2: Leonard, M. S.; Carroll, P. J.; Joullie, M. M. J. Org. Chem. 2004, 69, 2526.
28. (c) For entries 3 and 4: Tayama, E.; Saito, A.; Ooi, T.; Maruoka, K. Tetrahedron 2002, 58, 8307.
29. (d) For entry 5: Maruoka, K.; Banno, H.; Yamamoto, H. Tetrahedron: Asymmetry 1991, 2, 647.
30. (e) For entry 6: Faulkner, D. J.; Petersen, M. R. J. Am. Chem. Soc. 1973, 95, 553.