Synthesis of 2,3-trans disubstituted tetrahydrofurans through sequential xanthate radical addition-substitution reactions

Journal of Organic Chemistry

Volumn 71, Issue 6, 2006, Pages 2352-2359

  Jean Baptiste, Laëtitia ^a   Yemets, Sergiy ^a   Legay, Rémi ^a   Lequeux, Thierry ^a  

^a UNIVERSITÉ DE CAEN   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2,3-TRANS DISUBSTITUTED TETRAHYDROFURANS; 5-ALKYL DITHIOCARBONATES; C-BRANCHED NUCLEOSIDE ANALOGUES; CARBON-HETEROATOM BONDS; LEWIS ACID; NUCLEOPHILES; PRECURSOR; SEQUENTIAL XANTHATE RADICAL ADDITION-SUBSTITUTION REACTIONS; XANTHATES;

ACIDS; CARBONATES; CHEMICAL BONDS; DERIVATIVES; OLEFINS; SYNTHESIS (CHEMICAL);

FURAN RESINS;

2,3 DIHYDROFURAN DERIVATIVE; ALKENE DERIVATIVE; CARBONIC ACID DERIVATIVE; FURAN DERIVATIVE; LEWIS ACID; NUCLEOSIDE DERIVATIVE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG; XANTHIC ACID DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL BOND; CYCLIZATION; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

ALKENES; FREE RADICALS; FURANS; MOLECULAR STRUCTURE; STEREOISOMERISM; XANTHENES;

EID: 33645022446     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo052528y     Document Type: Article

References (64)

1. Matsuda, A.; Takenuki, K.; Sasaki, T.; Ueda, T. J. Med. Chem. 1991, 34, 234-239.
2. Lawrence, A. J.; Pavey, J. B. J.; Chan, M.; Fairhurst, R. A.; Collingwood, S. P.; Fisher, J.; Cosstick, R.; O'Neil, I. A. J. Chem. Soc., Perkin Trans. 1 1997, 2761-2767.
3. Lawrence, A. J.; Pavey, J. B. J.; Vortler, S.; Cosstick, R.; O'Neil, I. A. Org. Biomol. Chem. 2004, 2, 869-875.
4. (a) De Mesmaeker, A.; Häner, R.; Martin, P.; Moser, H. E. Acc. Chem. Res. 1995, 28, 366-374.
5. (b) Pattanayek, R.; Sethophong, L.; Pan, C.; Prhavc, M.; Prakash, T. P.; Manoharan, M.; Egli, M. J. Am. Chem. Soc. 2004, 126, 15006-15007.
6. (c) Prakash, T. P.; Allerson, C. R.; Dande, P.; Vickers, T. A.; Siuofi, N.; Jarres, R.; Baker, B. F.; Swayze, E. E.; Griffey, R. H.; Bhat, B. J. Med. Chem. 2005, 48, 4247-4253.
7. Ding, Y.; An, H.; Hong, Z.; Girardet, J. L. Bioorg. Med. Chem. Lett. 2005, 15, 725-727.
8. (a) Eldrup, A. B.; Allerson, C. R.; Bennett, C. F.; Bera, S.; Bhat, B.; Bhat, N.; Bosserman, M. R.; Brooks, J.; Burlein, C.; Carroll, S. S.; Cook, P. D.; Getty, K. L.; MacCoss, M.; MacMasters, D. R.; Olsen, D. B.; Prakash, T. P.; Prhavc, M.; Song, Q.; Tomassini, J. E.; Xia, J. J. Med. Chem. 2004, 47, 2283-2295.
9. (b) Bera, S.; Malik, L.; Bhat, B.; Carroll, S. S.; Hrin, R.; MacCoss, M.; MacMasters, D. R.; Miller, M. D.; Moyer, G.; Olsen, D. B.; Schleif, W. A.; Tomassini, J. E.; Eldrup, A. B. Bioorg. Med. Chem. 2004, 12, 6237-6247.
10. (a) Kvaerno, L.; Wengel, J. J. Chem. Soc., Chem. Commun. 2001, 1419-1424.
11. (b) Lesnik, E. A.; Guinosso, C. J.; Kawasaki, A. M.; Sasmor, H.; Zounes, M.; Cummins, L. L.; Ecker, D. J.; Cook, P. D.; Freirer, S. M. Biochemistry 1993, 32, 7832-7838.
12. (a) De Mesmaeker, A.; Lebreton, J.; Hoffmann, P.; Freier, S. M. Synlett 1993, 677-679.
13. (b) Velazquez, S.; Jimeno, M. L.; Huss, S.; Balzarini, J.; Camarasa, M. J. J. Org. Chem. 1994, 59, 7661-7670.
14. (c) Sukeda, M.; Shuto, S.; Sugimoto, I.; Ichikawa, S.; Matsuda, A. J. Org. Chem. 2000, 65, 8988-8996.
15. (d) Xi, Z.; Rong, J.; Chattopadhyaya, J. Tetrahedron 1994, 50, 5255-5272.
16. (e) Xi, Z.; Agback, P.; Plavec, J.; Sandström, A.; Chattopadhyaya, J. Tetrahedron 1992, 48, 349-370.
17. (a) Lawrence, A. J.; Pavey, J. B.; O'Neil, I. A.; Cosstick, R. Tetrahedron Lett. 1995, 36, 6341-6344.
18. (b) Lawrence, A. J.; Pavey, J. B.; Cosstick, R.; O'Neil, I. A. J. Org. Chem. 1996, 61, 9213-9222.
19. (a) Zard, S. Z. In Radical Reactions in Organic Synthesis; Oxford Chemistry Masters: Oxford, 2003.
20. (b) Zard, S. Z. Angew. Chem., Int. Ed. Engl. 1997, 36, 672-685.
21. (a) Kittaka, A.; Tanaka, H.; Odanaka, Y.; Ohnuki, K.; Yamaguchi, K.; Miyasaka, T. J. Org. Chem. 1994, 59, 3636-3641.
22. (b) Ogalino, J.; Mizunuma, H.; Kumamoto, H.; Takeda, S.; Haraguchi, K.; Nakamura, K. T.; Sugiyama, H.; Tanaka, H. J. Org. Chem. 2005, 70, 1684-1690.
23. (a) Marcotte, S.; Gérard, B.; Pannecoucke, X.; Feasson, C.; Quirion, J.-C. Synthesis 2001, 929-933.
24. (b) Lim, J.; Kim, Y. H. J. Chem. Soc., Perkin Trans. 1 1999, 3239-3241.
25. (a) Bertrand, F.; Pevere, V.; Quiclet-Sire, B.; Zard, S. Z. Org. Lett. 2001, 3, 1069-1071.
26. (b) Tournier, L.; Zard, S. Z. Tetrahedron Lett. 2005, 46, 455-459.
27. (c) Gagosz, F.; Zard, S. Z. Org. Lett. 2003, 5, 2655-2657.
28. Denieul, M.; Quiclet-Sire, B.; Zard, S. Z. J. Chem. Soc., Chem. Commun. 1996, 2511-2512.
29. (a) Zhang, X.; Qing, F.; Yu, Y. J. Org. Chem. 2000, 65, 7075-7082.
30. (b) Jeannot, F.; Gosselin, G.; Mathé, C. Org. Biomol. Chem. 2003, 1, 2096-2102.
31. (c) Dai, Q.; Piccirilli, J. A. Org. Lett. 2003, 5, 807-810.
32. (d) Li, N.; Tang, X.; Piccirilli, J. A. Org. Lett. 2001, 3, 1025-1028.
33. (a) Saito, A.; Ito, H.; Taguchi, T. Tetrahedron 2001, 57, 7487-7493.
34. (b) Murakami, S.; Ishii, H.; Fuchigami, T. J. Fluorine Chem. 2004, 125, 609-614.
35. (a) Udding, J. H.; Hiemstra, H.; Speckamp, W. N. J. Org. Chem. 1994, 59, 3721-3725.
36. (b) Liard, A.; Quiclet-Sire, B.; Saicic, R. N.; Zard, S. Z. Tetrahedron Lett. 1997, 38, 1759-1762.
37. (c) Maslak, V.; Cekovic, Z.; Saicic, R. N. Synlett 1998, 1435-1437.
38. Xiao, F.; Wu, F.; Shen, Y.; Zhou, L. J. Fluorine Chem. 2005, 126, 63-67.
39. (a) Della, E. W. J. Am. Chem. Soc. 1967, 89, 5221-5224.
40. (b) Seebach, D. Angew. Chem., Int. Ed. Engl. 1990, 29, 1320-1327.
41. (c) Schlosser, M.; Michel, D. Tetrahedron 1996, 52, 99-108.
42. (d) O'Hagan, D.; Rzepa, H. S. J. Chem. Soc., Chem. Commun. 1997, 645-652.
43. (a) Miura, K.; Ichinose, Y.; Nozaki, K.; Fugami, K.; Oshima, K. Utimoto, K. Bull. Chem. Soc. Jpn. 1989, 62, 143-147.
44. (b) Ollivier, C. Renaud, P. Chem. Rev. 2001, 101, 3415-3434.
45. (c) Perchyonok, V. T. Schiesser, C. H. Tetrahedron Lett. 1998, 39, 5437-5438.
46. (d) Briggs, M. E.; Zard, S. Z. Synlett 2005, 334-336.
47. (a) Quiclet-Sire, B.; Zard, S. Z. J. Am. Chem. Soc. 1996, 118, 9190-9191.
48. (b) Studer, A.; Amrein, S. Synthesis 2002, 835-849.
49. Legrand, N.; Quiclet-Sire, B.; Zard, S. Z. Tetrahedron Lett. 2000, 41, 9815-9818.
50. Perchyonok, V. T.; Schiesser, C. H. Tetrahedron Lett. 1998, 39, 5437-5438.
51. (a) Bogusiak, J.; Szeja, W. Carbohydr. Res. 1996, 295, 235-243.
52. (b) Bogusiak, J.; Szeja, W. Carbohydr. Res. 2001, 330, 141-144.
53. (a) Doane, W. M.; Shasha, B. S.; Russell, C. R.; Rist, C. E. J. Org. Chem. 1967, 32, 1080-1083.
54. (b) Szeja, W.; Bogusiak, J. Carbohydr. Res. 1987, 170, 235-239.
55. (c) Hürzeler, M.; Bernet, B.; Vasella, A. Helv. Chim. Acta 1993, 76, 995-1011.
56. Franck, X.; Hocquemiller, R.; Figadère, B. J. Chem. Soc., Chem. Commun. 2002, 160-161.
57. (a) Smith, D. M.; Woerpel, K. A. Org. Lett. 2004, 6, 2063-2066.
58. (b) Colby, E. A.; O'Brien, K. C.; Jamison, T. F. J. Am. Chem. Soc. 2005, 127, 4297-4307.
59. (c) Larsen, C. H.; Ridgway, B. H.; Shaw, J. T.; Woerpel, K. A. J. Am. Chem. Soc. 1999, 121, 12208-12209.
60. (a) Shimomura, N.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1994, 67, 2532-2534.
61. (b) Shimomura, N.; Matsutani, T.; Mukaiyama, T. Bull Chem. Soc. Jpn. 1994, 67, 3100-3106.
62. (c) Shimomura, N.; Mukaiyama, T. Chem. Lett. 1993, 1941-1944.
63. Cameron, M. A.; Cush, S. B.; Hammer, R. P. J. Org. Chem. 1997, 62, 9065-9069.
64. Claridge, T. D. W. In High-Resolution NMR Techniques in Organic Chemistry; Tetrahedron Organic Chemistry Series; Oxford: Oxford, 1999; Vol. 10, Chapter 8.