2-(Trimethylsilyloxy)furan as a dianion equivalent: A two-step synthesis of functionalized spirocyclic butenolides

Organic Letters

Volumn 8, Issue 17, 2006, Pages 3705-3707

  Maulide, Nuno ^a   Markó, István E ^a  

^a UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748622297     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061284g     Document Type: Article

References (32)

1. (a) Langer, P.; Albrecht, U. Synlett 2002, 11, 1841.
2. (b) Wenderborn, S.; Binot, G.; Nina, M.; Winkler, T. Synlett 2002, 10, 1683.
3. (c) Rauter, A. P.; Figueiredo, J.; Ismael, M.; Canda, T.; Font, J.; Figueredo, M. Tetrahedron: Asymmetry 2001, 12, 1131.
4. (d) Paquette, L. A.; Owen, D. R.; Bibart, R. T.; Seekamp, C. K.; Kahane, A. L.; Lanter, J. C.; Corral, M. A. J. Org. Chem. 2001, 66, 2828.
5. (e) Michaut, M.; Santelli, M.; Parrain, J.-L. J. Organomet. Chem. 2000, 606, 93.
6. (f) Hoffmann, H. M. R.; Wulferding, A. Synlett 1993, 6, 415.
7. (g) Orduna, A.; Gerardo Zepeda, L.; Tamariz, J. Synthesis 1993, 4, 375.
8. (h) Black, T. H.; McDermott, T. S.; Brown, G. A. Tetrahedron Lett. 1991, 32, 6501.
9. (i) Ortuno, R. M.; Corbera, J.; Font, J. Tetrahedron Lett. 1986, 27, 1081.
10. (j) Canonne, P.; Belanger, D.; Lemay, G. J. Org. Chem. 1982, 47, 3953.
11. (k) Caine, D.; Smith, T. L. Synth. Commun. 1980, 10, 751.
12. (l) Iwai, K.; Kosugi, H.; Miyazaki, A.; Hisashi, U. Synth. Commun. 1976, 6, 357 and references herein.
13. For a recent example of the synthesis of aza-spirobutenolides through an unusual strategy, see: (m) Guindeuil, S.; Zard, S. Z. Chem. Commun. 2006, 665.
14. Liu, T.-X. Crop Prot. 2004, 23, 505.
15. Iida, T.; Satoh, H.; Maeda, K.; Yamamoto, Y.; Asakawa, K.-i.; Sawada, N.; Wada, T.; Kadowaki, C.; Itoh, T.; Mase, T.; Weissman, S. A.; Tschaen, D.; Krska, S.; Volante, R. P. J. Org. Chem. 2005, 70, 9222.
16. Reddy, N. S.; Venkatesham, U.; Rao, T. P.; Venkateswarlu, Y. Ind. J. Chem., Sect. B 2000, 39, 393.
17. Murakami, T.; Morikawa, Y.; Hashimoto, M.; Okuno, T.; Harada, Y. Org. Lett. 2004, 6, 157.
18. (a) Markó, I. E.; Vanherck, J.-C.; Ates, A.; Tinant, B.; Leclercq, J.-P. Tetrahedron Lett. 2003, 44, 3333.
19. For an application to total synthesis, see: (b) Maulide, N.; Vanherck, J.-C.; Markó, I. E. Eur. J. Org. Chem. 2004, 3962.
20. Maulide, N.; Markó, I. E. Chem. Commun. 2006, 1200.
21. For reviews on the chemistry of trimethylsilyloxyfuran derivatives, see: (a) Casiraghi, G.; Rassu, G. Synthesis 1995, 607.
22. (b) Bur, S. K.; Martin, S. F. Tetrahedron 2001, 57, 3211.
23. For a rare example of aldol-mediated spirocyclization, see: (a) Kende, A. S.; Hernando, J. I. M.; Milbank, J. B. J. Tetrahedron 2002, 58, 61.
24. For Mannich-based spirocyclizations, see: (b) Tokumaru, K.; Arai, S.; Nishida, A. Org. Lett. 2006, 8, 27.
25. (c) Martin, S. F.; Bur, S. K. Tetrahedron Lett. 1997, 38, 7641.
26. For a related cyclization, see: (d) Kobayashi, K.; Itoh, M.; Suginome, H. Tetrahedron Lett. 1987, 28, 3369.
27. Pelter, A.; Al-Bayati, R. I. H.; Ayoub, M. T.; Lewis, W.; Pardasani, P.; Hansel, R. J. Chem. Soc., Perkin Trans. 1 1987, 4, 717.
28. (a) Khurana, J. M.; Sharma, P. Bull. Chem. Soc. Jpn. 2004, 549.
29. (b) George, A.; Schulte, M.; Reiser, O. J. Org. Chem. 2006, 71, 2173.
30. (a) Shing, T. K. M.; Tam, E. K. W.; Tai, V. W.-F.; Chung, I. H. F.; Jiang, Q. Chem.-Eur. J. 1996, 2, 50.
31. See also: (b) Paquette, L. A.; Seekamp, C. K.; Kahane, A. L.; Hilmey, D. G.; Galucci, J. J. Org. Chem. 2004, 69, 7443.
32. Dong, S.; Paquette, L. A. J. Org. Chem. 2006, 71, 1647 and references therein.