Synthesis of cycloheptane-1,2,3,4-tetraols as cyclitol mimetics

Journal of Chemical Research

Volumn , Issue 6, 2005, Pages 382-384

  Şengül, Mehmet Emin ^a   Menzek, Abdullah ^a   Saraçoǧlu, Nurullah ^a  

^a ATATÜRK UNIVERSITY   (Turkey)

Author keywords

Carbasugar; Conduritol; Cyclitol; Endoperoxide; Inositol

Indexed keywords

EID: 22444437880     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/0308234054506794     Document Type: Article

References (39)

1. (a) Y. Chapleur (Ed.), Carbohydrate Mimics, (Wiley-VCH Weinheim oder John Wiley & Sons New York) Wiley-VCH, New York, 1998, 87-258;
2. (b) M. Kummeter and U. Kazmaier, Eur. J. Org. Chem., 2003, 3325;
3. (c) Last review for cyclitols: M.S. Gültekin, M. Çelik and M. Balci, Curr. Org. Chem., 2004, 8, 1159.
4. (a) S. Ogawa, In Carbohydrates in Drug Design; Z.J. Witezak and K.A. Nieforth, Eds.; Dekker: New York, 1997, p. 433;
5. (b) Y. Bleriot, A. Giroult, J.-M. Mallet, E. Rodriguez, P. Vogel and P. Sinay, Tetrahedron: Asymmetry, 2002, 13, 2553 and refs cited therein.
6. (a) T.D. Heightman and A.T. Vasella, Angew. Chem., Int. Ed. Engl., 1999, 38, 750;
7. (b) G.S. Jacob, Curr. Opin. Struct. Biol., 1995, 5, 605;
8. (c) T. Suami and S. Ogawa, Adv. Carbohydr. Chem. Biochem., 1990, 48, 21;
9. (d) T. Suami, Top. Curr. Chem., 1990, 154, 257.
10. (a) M. Balci, Y. Sütbeyaz and H. Seçen, Tetrahedron, 1990, 46, 3715;
11. (b) T. Hudlicky, D.A. Entwistle, K.K. Pitzer and A.J. Thorpe, Chem. Rev., 1996, 96, 1195;
12. (c) T. Suami, Pure Appl. Chem., 1987, 59, 1509;
13. (d) M. Balci, Pure Appl. Chem., 1997, 69, 97;
14. (e) G. Mehta, N. Mohal and S. Lakshminath, Tetrahedron Lett., 2000, 41, 3505.
15. (a) M.J. Berridge, Nature, 1993, 361, 315 and refs cited therein;
16. (b) T. Hudlicky, N. Restrepo-Sanchez, P.D. Kary and L.M. Jaramillo-Gomez, Carbohydr. Res. 2000, 324, 200.
17. (a) G. Mehta and D.S. Reddy, Tetrahedron Lett., 1999, 40, 9137;
18. (b) G. Mehta, D.S. Reddy, S.S. Ramesh and U. Tatu, Tetrahedron Lett., 1999, 40, 9141;
19. (c) G. Mehta and S.S. Ramesh, Chem. Commun., 2000, 2429.
20. For a few related examples of syntheses of annulated conduritols, see: (a) D.C. Billington, F. Perron-Sierra, I. Picard, S. Beaubras, J. Duhault, J. Espinal and S. Challal, Bioorg. Med. Chem. Lett., 1994, 4, 2307;
21. (b) Y. Kara, M. Balci, S.A. Bourne and W.H. Watson, Tetrahedron Lett., 1994, 35, 3349;
22. (c) M. Desjardins, M.C. Lallemand, T. Hudlicky and K.A. Abboud, Synlett, 1997, 728.
23. (a) G. Mehta and S.S. Ramesh, Chem. Commun., 2000, 2429;
24. (b) G. Mehta and S.S. Ramesh, Tetrahedron Lett., 2001, 42, 1987.
25. (a) Z. Zeying and Z. Mingzhe, Jiegou Huaxue, 1987, 6, 128;
26. (b) Chem. Abs., 1988, 108, 167846r.
27. H. Seçen, M.S. Gültekin, Y. Sütbeyaz and M. Balci, Turk. J. Chem., 1993, 17, 108.
28. (a) J. Marco-Contelles and E. de Opazo, J. Org. Chem., 2003, 67, 3705;
29. (b) J. Marco-Contelles and E. de Opazo, Tetrahedron Lett., 2000, 41, 2439;
30. (c) I. Hanna and L. Ricard, Org. Lett., 2000, 2, 2651.
31. (a) M. Balci, Chem. Rev., 1981, 81, 91;
32. (b) S.J. Bis, D.T. Whitaker and C.R. Johnson, Tetrahedron: Asymmetry, 1993, 4, 875;
33. (c) A.C. Cope, T.A. Liss and G.W. Wood, J. Am. Chem. Soc., 1957, 79, 6287.
34. For similar reasons, see: N. Akbulut and M. Balci, J. Org. Chem., 1988, 53, 3338.
35. For di-O-isopropylidene and tetrabenzoate derivatives of 13, see: H. Redlich, W. Sudau, A.K. Szardenings and R. Vollerthun, Carbohydr. Res., 1992, 226, 57.
36. (a) E. Sisu, M. Sollogoub, J.-M. Mallet and P. Sinay, Tetrahedron, 2002, 58, 10189;
37. (b) F.-D. Boyer and J.-Y. Lallemand, Tetrahedron, 1994, 50, 10443;
38. (c) A.J. Pearson and S. Katiyar, Tetrahedron, 2000, 56, 2297;
39. (d) O. Duclos, M. Mondange, A. Duréault and J.C. Depezay, Tetrahedron Lett., 1992, 33, 8061;