Synthesis of β,γ,γ-tri- or γ,γ-disubstituted α-methylene-γ-butyrolactones starting from the Baylis-Hillman adducts

Bulletin of the Korean Chemical Society

Volumn 27, Issue 9, 2006, Pages 1489-1492

  Ka, Young Lee ^a   Da, Yeon Park ^a   Jae, Nyoung Kim ^a  

^a Chonnam National University   (South Korea)

Author keywords

Baylis Hillman adducts; Indium; Methylene butyrolactones

Indexed keywords

EID: 33749022750     PISSN: 02532964     EISSN: 12295949     Source Type: Journal    
DOI: 10.5012/bkcs.2006.27.9.1489     Document Type: Article

References (35)

1. For the synthesis of lactones via indium-mediated reactions, see: (a) Paquette, L. A.; Mendez-Andino, J. Tetrahedron Lett. 1999, 40, 4301.
2. (b) Choudhury, P. K.; Foubelo, F.; Yus, M. Tetrahedron Lett. 1998, 39, 3581.
3. (c) Loh, T.-P.; Lye, P.-L. Tetrahedron Lett. 2001, 42, 3511.
4. Zinc-mediated synthesis of lactones: Lee, K.-H.; Ibuka, T.; Kim, S.-H.; Vestal, B. R.; Hall, I. H. J. Med. Chem. 1975, 18, 812.
5. Synthesis of lactones involving cross-coupling/allylboration protocol: Kabalka, G. W.; Venkataiah, B.; Chen, C. Tetrahedron Lett. 2006, 47, 4187.
6. Further references on the synthesis and biological activities of α-methylene-γ-butyrolactones, see: (a) Sidduri, A.-R.; Knochel, P. J. Am. Chem. Soc. 1992, 114, 7579.
7. (b) Sidduri, A.-R.; Rozema, M. J.; Knochel, P. J. Org. Chem. 1993, 58, 2694.
8. (c) Peng, H.; Kim, D.-I.; Sarkaria, J. N.; Cho, Y.-S.; Abraham, R. T.; Zalkow, L. H. Bioorg. Med. Chem. 2002, 10, 167.
9. (d) Nozaki, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1987, 60, 3465.
10. (e) Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 898.
11. (f) Kennedy, J. W. J.; Hall, D. G. J. Am. Chem. Soc. 2002, 124, 11586.
12. (g) Kennedy, J. W. J.; Hall, D. G. J. Org. Chem. 2004, 69, 4412.
13. For the synthesis of natural products containing α-methylene- γ-butyrolactone skeleton having another carboxylic acid group, see: (a) Ghatak, A.; Sarkar, S.; Ghosh, S. Tetrahedron 1997, 53, 17335.
14. (b) Sarkar, S.; Ghosh, S. Tetrahedron Lett. 1996, 37, 4809.
15. (c) Mandal, P. K.; Maiti, G.; Roy, S. C. J. Org. Chem. 1998, 63, 2829.
16. (d) Saicic, R. N.; Zard, S. Z. Chem. Commun. 1996, 1631.
17. (e) Maiti, G.; Roy, S. C. J. Chem. Soc., Perkin Trans. 1 1996, 403.
18. (f) Hon, Y.-S.; Hsieh, C.-H.; Liu, Y.-W. Tetrahedron 2005, 61, 2713.
19. (g) Bella, M.; Margarita, R.; Orlando, C.; Orsini, M.; Parlanti, L.; Piancatelli, G. Tetrahedron Lett. 2000, 41, 561.
20. (h) Drioli, S.; Felluga, F.; Forzato, C.; Nitti, P.; Pitacco, G.; Valentin, E. J. Org. Chem. 1998, 63, 2385.
21. (i) Pohmakotr, M.; Harnying, W.; Tuchinda, P.; Reutrakul, V. Helv. Chim. Acta 2002, 85, 3792.
22. (j) Biel, M.; Kretsovali, A.; Karatzali, E.; Papamatheakis, J.; Giannis, A. Angew. Chem. Int. Ed. 2004, 43, 3974.
23. (k) Srikrishna, A. J. Chem. Soc., Chem. Commun. 1987, 587.
24. For the indium-mediated reactions in the Baylis-Hillman chemistry, see: (a) Isaac, M. B.; Paquette, L. A. J. Org. Chem. 1997, 62, 5333.
25. (b) Paquette, L. A.; Bennett, G. D.; Chhatriwalla, A.; Isaac, M. B. J. Org. Chem. 1997, 62, 3370.
26. (c) Paquette, L. A.; Bennett, G. D.; Isaac, M. B.; Chhatriwalla, A. J. Org. Chem. 1998, 63, 1836.
27. (d) Paquette, L. A.; Rothhaar, R. R.; Isaac, M.; Rogers, L. M.; Rogers, R. D. J. Org. Chem. 1998, 63, 5463.
28. (e) Choudhury, P. K.; Foubelo, F.; Yus, M. J. Org. Chem. 1999, 64, 3376.
29. (a) Kang, S.-K.; Baik, T.-G.; Jiao, X.-H. Synth. Commun. 2002, 32, 75.
30. (b) Reddy, G. V.; Rao, G. V.; Iyengar, D. S. Tetrahedron Lett. 1999, 40, 3937.
31. (c) Kamal, A.; Reddy, G. S. K.; Reddy, K. L. Tetrahedron Lett. 2001, 42, 6969.
32. (a) Lee, M. J.; Kim, S. C.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 140.
33. (b) Lee, K. Y.; Kim, S. C.; Kim, J. N. Bull. Korean Chem. Soc. 2006, 27, 319.
34. (c) Lee, K. Y.; Kim, S. C.; Kim, J. N. Tetrahedron Lett. 2006, 47, 977.
35. (d) Lee, K. Y.; Seo, J.; Kim, J. N. Tetrahedron Lett. 2006, 47, 3913.