A new synthesis of carbapentofuranoses from carbohydrates

Tetrahedron Letters

Volumn 38, Issue 35, 1997, Pages 6189-6192

  Désiré, Jérôme ^a   Prandi, Jacques ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAPENTOFURANOSE DERIVATIVE; CARBOHYDRATE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0040807680     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01395-6     Document Type: Article

References (31)

1. Renoux, J.-M.; Rohmer, M. Eur. J. Biochem. 1985, 151, 405-410. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210. Adinolfi, M.; Corsaro, M. M.; De Castro, C.; Evidente, A.; Lanzetta, R.; Molinaro, A.; Parrilli, M. Carbohydrate Res. 1996, 284, 111-118.
2. Renoux, J.-M.; Rohmer, M. Eur. J. Biochem. 1985, 151, 405-410. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210. Adinolfi, M.; Corsaro, M. M.; De Castro, C.; Evidente, A.; Lanzetta, R.; Molinaro, A.; Parrilli, M. Carbohydrate Res. 1996, 284, 111-118.
3. Renoux, J.-M.; Rohmer, M. Eur. J. Biochem. 1985, 151, 405-410. Winchester, B.; Fleet, G. W. J. Glycobiology 1992, 2, 199-210. Adinolfi, M.; Corsaro, M. M.; De Castro, C.; Evidente, A.; Lanzetta, R.; Molinaro, A.; Parrilli, M. Carbohydrate Res. 1996, 284, 111-118.
4. Agrofoglio, L.; Suhas, E.; Farese, A.; Condom, R.; Challand, S. R.; Earl, S. R.; Guedj, R. Tetrahedron 1994, 50, 10611-10670.
5. a) Tadano, K.; Maeda, H.; Hoshino, M.; Iimura, Y.; Suami, T. Chem. Lett. 1986, 1081-1084.
6. b) Tadano, K.; Hoshino, M.; Ogawa, S.; Suami, T. J. Org. Chem. 1988, 53, 1427-1432.
7. Yoshikawa, M.; Cha B. C.; Okaichi, Y.; Kitagawa, I. Chem. Pharm. Bull. 1988, 36, 3718-3721.
8. Tadano, K.; Hakuba, K.; Kimura, H.; Ogawa, S. J. Org. Chem. 1989, 54, 276-279.
9. e) Yoshikawa, M.; Murakami, N.; Inoue, Y.; Hatakeyama, S.; Kitagawa, I. Chem. Pharm. Bull. 1993, 41, 636-638.
10. f) Yoshikawa, M.; Yokokawa, Y.; Inoue, Y.; Yamaguchi, S.; Murakami, N. Tetrahedron 1994, 33, 9961-9974
11. Parry, R. J.; Haridas, K.; De Jong, R.; Johnson, C. R. Tetrahedron Lett. 1990, 31, 7549-7552.
12. a) Marschner, C.; Penn, G.; Griengl, H. Tetrahedron Lett. 1990, 31, 2873-2874.
13. b) Marschner, C.; Baumgartner, J.; Griengl, H. J. Org. Chem. 1995, 60, 5224-5235.
14. Chénédé, A.; Pothier, P.; Sollogoub, M.; Fairbanks, A. J.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1995, 1373-1374. Cronjé Grové, J. J.; Holzapfel, C. W.; Williams, D. B. G.; Tetrahedron Lett. 1996, 37, 1305-1308. Chiara, J. L.; Martinez, S.; Bernabé, M. J. Org. Chem. 1996, 61, 6488-6489.
15. Chénédé, A.; Pothier, P.; Sollogoub, M.; Fairbanks, A. J.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1995, 1373-1374. Cronjé Grové, J. J.; Holzapfel, C. W.; Williams, D. B. G.; Tetrahedron Lett. 1996, 37, 1305-1308. Chiara, J. L.; Martinez, S.; Bernabé, M. J. Org. Chem. 1996, 61, 6488-6489.
16. Chénédé, A.; Pothier, P.; Sollogoub, M.; Fairbanks, A. J.; Sinaÿ, P. J. Chem. Soc., Chem. Commun. 1995, 1373-1374. Cronjé Grové, J. J.; Holzapfel, C. W.; Williams, D. B. G.; Tetrahedron Lett. 1996, 37, 1305-1308. Chiara, J. L.; Martinez, S.; Bernabé, M. J. Org. Chem. 1996, 61, 6488-6489.
17. Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990-2016. Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 2400-2410.
18. Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 1990-2016. Bernet, B.; Vasella, A. Helv. Chim. Acta 1979, 62, 2400-2410.
19. Nakamura, E.; Inubushi, T.; Aoki, S.; Machii, D. J. Am. Chem. Soc. 1991, 113, 8980-8982. Mayer, S.; Prandi, J. Tetrahedron Lett. 1996, 37, 3117-3120.
20. Nakamura, E.; Inubushi, T.; Aoki, S.; Machii, D. J. Am. Chem. Soc. 1991, 113, 8980-8982. Mayer, S.; Prandi, J. Tetrahedron Lett. 1996, 37, 3117-3120.
21. Bamhaoud, T.; Prandi, J. J. Chem. Soc., Chem. Commun. 1996, 1299-1230.
22. See Figure 1 for numbering of glycosides I, hexenitols derivatives III and carbafuranoses IV .
23. Garegg, P. J.; Samuelsson, B. J. Chem. Soc., Chem. Commun. 1979, 979-980.
24. Gray, G. R.; Hartman, F. C.; Barker, R. J. Org. Chem. 1965, 30, 2020-2024. Martin, O. R.; Yang, F.; Xie, F. Tetrahedron Lett. 1995, 36, 47-50.
25. Gray, G. R.; Hartman, F. C.; Barker, R. J. Org. Chem. 1965, 30, 2020-2024. Martin, O. R.; Yang, F.; Xie, F. Tetrahedron Lett. 1995, 36, 47-50.
26. Floriani, C.; Calderazzo, F. J. Chem. Soc. A 1969, 946-953.
27. 23 +4.1 for the enantiomer.
28. Beckwith, A. L. J. Tetrahedron 1981, 37, 3073-3100. Beckwitn, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925-3941.
29. Beckwith, A. L. J. Tetrahedron 1981, 37, 3073-3100. Beckwitn, A. L. J.; Schiesser, C. H. Tetrahedron 1985, 41, 3925-3941.
30. RajanBabu, T. V. Acc. Chem. Res. 1991, 24, 139-145.
31. For a literature example of almost complete oxygenation of an uncyclized 5-hexenyl radical, see : Quirk, R.P.; Lea, R.E. J. Am. Chem. Soc. 1976, 98, 5973-5978.