Efficient synthesis of (E)-3-alkylidene-2(3H)-furanones from 3-(1-hydroxyalkyl)-2-silyloxyfurans

Synlett

Volumn , Issue 10, 2006, Pages 1511-1514

  Boukouvalas, John ^a   Marion, Olivier ^a  

^a UNIVERSITÉ LAVAL   (Canada)

Author keywords

2 silyloxyfurans; Bromination; Lactones; Lithiation; Stereoselectivity

Indexed keywords

2 TRIISOPROPYLSILYLOXY 3 BROMOFURAN; ALDEHYDE DERIVATIVE; FURAN DERIVATIVE; FURANONE DERIVATIVE; HALIDE; LITHIUM; UNCLASSIFIED DRUG;

ANION EXCHANGE; ARTICLE; BROMINATION; CHROMATOGRAPHY; DRUG STRUCTURE; DRUG SYNTHESIS; ELIMINATION REACTION;

EID: 33745712078     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-944202     Document Type: Article

References (47)

1. (a) Okabe, T.; Yoshida, E.; Chieda, S.; Endo, K.; Kamiya, S.; Osada, K.; Tanaka, S.; Okura, A.; Suda, H. J. Antibiotics 1994, 47, 289.
2. (b) Tanaka, S.; Okabe, T.; Nakajima, S.; Yoshida, E.; Suda, H. J. Antibiotics 1994, 47, 294.
3. (c) Tanaka, S.; Okabe, T.; Nakajima, S.; Yoshida, E.; Morishima, H. J. Antibiotics 1994, 47, 297.
4. (a) Chang, R. S.; Ding, L.; Gai-Qing, C.; Qi-Choa, P.; ZeLin, Z.; Smith, K. M. Proc. Soc. Exp. Biol. Med. 1991, 197, 59.
5. (b) Basak, A.; Cooper, S.; Roberge, A. G.; Banik, U. K.; Chrétien, M.; Seidah, N. G. Biochem. J. 1999, 338, 107.
6. (c) Basak, A.; Zhong, M.; Munzer, J. S.; Chrétien, M.; Seidah, N. G. Biochem. J. 2001, 353, 537.
7. (a) Kitagawa, I.; Simanjuntak, P.; Hori, K.; Nagami, N.; Mahmud, T.; Shibuya, H.; Kobayashi, M. Chem. Pharm. Bull. 1994, 42, 1050.
8. 1 has not been assigned.
9. Yadav, R. D.; Kataky, J. C. S.; Mathur, R. K. Indian J. Chem., Sect B: Org. Chem. Incl. Med. Chem. 1999, 38, 248.
10. Janeki, T.; Blaszczyk, E.; Studzian, K.; Janecka, A.; Krajewska, U.; Rózalski, M. J. Med. Chem. 2005, 48, 3516; and references therein.
11. Rao, Y. S. Chem. Rev. 1976, 76, 625.
12. Shanmugasundaram, M.; Raghunathan, R.; Malar, E. J. P. Heteroat. Chem. 1998, 9, 517.
13. Rischmann, M.; Mues, R.; Geiger, H.; Laas, H. J.; Eicher, T. Phytochemistry 1989, 28, 867.
14. Egorova, A. Y. Russ. Chem. Bull., Int. Ed. 2002, 51, 183.
15. Khan, R. H.; Rastogi, R. C. J. Chem. Res., Synop. 1991, 260.
16. (a) Shurov, S. N.; Zhikina, I. A.; Podvintsev, I. B. Russ. J. Org. Chem. 2002, 38, 862.
17. (b) See also: Shurov, S. N.; Zhikina, I. A. Russ. J. Gen. Chem. 2000, 70, 1779.
18. Nair, V.; Bindu, S.; Sreekumar, V.; Rath, N. P. Org. Lett. 2003, 5, 665.
19. (a) Huang, Y.; Alper, H. J. Org. Chem. 1991, 56, 4534.
20. (b) See also: El Ali, B.; Alper, H. Synlett 2000, 161.
21. Rossi, R.; Bellina, F.; Bechini, C.; Mannina, L.; Vergamini, P. Tetrahedron 1998, 54, 135.
22. Lim, S.-G.; Kwon, B.-I.; Choi, M.-G.; Jun, C.-H. Synlett 2005, 1113.
23. (a) Sigman, M. S.; Kerr, C. E.; Eaton, B. E. J. Am. Chem. Soc. 1993, 115, 7545.
24. (b) Trifonov, L. S.; Orahovats, A. S.; Linden, A.; Heimgartner, H. Helv. Chim. Acta 1992, 75, 1872.
25. (a) Ochoa de Echagüen, C.; Ortuño, R. M. Tetrahedron 1994, 50, 12457.
26. (b) Grossmann, G.; Poncioni, M.; Bornand, M.; Jolivet, B.; Neuburger, M.; Séquin, U. Tetrahedron 2003, 59, 3237.
27. (c) Posner, G. H.; Afarinkia, K.; Dai, H. Org. Synth. 1995, 73, 231.
28. (a) Bromofuranone 9 has been previously prepared in three steps from 2,5-dimethoxy-2,5-dihydrofuran: Bella, M.; Piancatelli, G.; Squarcia, A. Tetrahedron 2001, 57, 4429; and references therein.
29. (b) See also: Vaz, B.; Alvarez, R.; Brückner, R.; de Lera, A. R. Org. Lett. 2005, 7, 545.
30. Boukouvalas, J.; Lachance, N. Synlett 1998, 31.
31. For the preparation and addition of metallated silyloxyfurans to carbonyl compounds, see: (a) Boukouvalas, J.; Cheng, Y.-X.; Robichaud, J. J. Org. Chem. 1998, 63, 228.
32. (b) Kanoh, N.; Ishihara, J.; Yamamoto, Y.; Murai, A. Synthesis 2000, 1878.
33. (c) Xin, Z.; Zheng, G. Z.; Stewart, A. O. Synlett 2000, 1324.
34. (d) Sibi, M. P.; He, L. Org. Lett. 2004, 6, 1749.
35. (e) Paintner, F. F.; Allmendinger, L.; Bauschke, G. Synlett 2005, 2735.
36. +]; found: 318.0656.
37. +]; found: 392.1890.
38. 1H NMR from their E-isomers by the upfield shift of the three olefin protons (Δδ ca. 0.1-0.3 ppm).
39. +]; found: 162.0322.
40. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841.
41. (a) Wollenberg, R. H. Tetrahedron Lett. 1980, 21, 3139.
42. (b) Tanaka, K.; Terauchi, M.; Kaji, A. Bull. Chem. Soc. Jpn. 1982, 55, 3935.
43. (c) Chen, S.-Y.; Joullié, M. M. Tetrahedron Lett. 1983, 24, 5027.
44. For alternative routes to 3-alkenylfuranones, see: (a) Yu, W.-Y.; Alper, H. J. Org. Chem. 1997, 62, 5684.
45. (b) Dixon, D. J.; Ley, S. V.; Reynolds, D. J. Angew. Chem. Int. Ed. 2000, 39, 3622.
46. (c) Johansson, M.; Köpeke, B.; Anke, H.; Sterner, O. Tetrahedron 2002, 58, 2523.
47. (d) Oh, C. H.; Park, S. J.; Ryu, J. H.; Gupta, A. K. Tetrahedron Lett. 2004, 45, 7039.