Stereocontrolled construction of tetrasubstituted tetrahydrofurans: Synthesis of 2,5-anhydro d-glucitol

Tetrahedron Letters

Volumn 51, Issue 46, 2010, Pages 6011-6013

  Das, Biswanath ^a   Kumar, Duddukuri Nandan ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

2,3 Epoxy alcohol; 2,5 Anhydro d glucitol; 5 endo tet Cyclization; Tetrasubstituted tetrahydrofuran

Indexed keywords

2,5 ANHYDRO DEXTRO GLUCITOL; CIS BUT 2 ENE 1,4 DIOL; NUCLEOPHILE; SORBITOL; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 77958009551     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.049     Document Type: Article

References (31)

1. M.M. Faul, and B.E. Huff Chem. Rev. 100 2000 2407
2. A. Bermejoj, B. Figadere, M.C. Zafrapolo, I. Barrachina, E. Estomell, and D. Cortes Nat. Prod. Rep. 22 2005 269
3. M. Saleem, H.J. Kim, M.S. Ali, and Y.S. Lee Nat. Prod. Rep. 22 2005 696
4. E.J. Kang, and E. Lee Chem. Rev. 105 2005 4348
5. G. Cardillo, and M. Orena Tetrahedron 46 1990 3321
6. J.C. Harmage, and B. Figadere Tetrahedron: Asymmetry 4 1993 1711
7. U. Koert Synthesis 1995 115
8. T.K. Chakraborty, S. Jayaprakash, P.V. Diwan, R. Nagaraj, S.R.B. Jampani, and A.C. Kunwar J. Am. Chem. Soc. 120 1998 12962
9. K. Miura, and A. Hosomi Synlett 2003 143
10. J.P. Wolfe, and M.B. Hay Tetrahedron 63 2007 261
11. T.J. Donohoe, O. Williams, and G.H. Churchill Angew. Chem., Int. Ed. 47 2008 2869
12. G.K. Friestad, and H.J. Lee Org. Lett. 11 2009 3958
13. H. Aurodox-Maehr, M. Leach, T.H. Williams, W. Benz, and J.F. Blount J. Am. Chem. Soc. 95 1973 8448
14. R.S. Dewey, B.H. Arison, J. Hannah, D.H. Shih, and G. Albers-Schonberg J. Antibiot. 38 1985 1691
15. R.E. Dolle, and K.C. Nicolaou J. Am. Chem. Soc. 107 1985 1691
16. R.E. Dolle, and K.C. Nicolaou J. Am. Chem. Soc. 107 1985 1693
17. J.E. Baldwin Chem. Commun. 1976 734
18. J.E. Baldwin, J. Cutting, W. Dupont, L. Kruse, L. Silberman, and R.C. Thomas Chem. Commun. 1976 736
19. J.E. Baldwin, R.C. Thomas, L.I. Kruse, and L. Silberman J. Org. Chem. 42 1977 3846
20. M. Karikomi, S. Watanabe, Y. Kimura, and T. Uyehara Tetrahedron Lett. 43 2002 1495
21. H.D. Doan, J. Gallon, A. Piou, and J.-M. Vatele Synlett 2007 983
22. B. Kang, J. Mowat, T. Pinter, and R. Britton Org. Lett. 11 2009 1717
23. R. Persky, and A. Albeck J. Org. Chem. 65 2000 5632
24. J.A. Bennek, and G.R. Gray J. Org. Chem. 67 2002 8862
25. T. Donohoe, and S. Butterworth Angew. Chem., Int. Ed. 42 2003 8
26. E. Hungerbuhelr, and D. Seebach Helv. Chim. Acta 64 1984 687
27. D. Seyforth, and L.G. Vaughau J. Organomet. Chem. 1 1963 138
28. I. Izzo, M. Scioscia, P. Del Gaudio, and F. De Riccardis Tetrahedron Lett. 42 2001 5421
29. R.C. Cookson, and S.R. Wallis J. Chem. Soc. B 1966 1245
30. C. Poulard, J. Carnet, S. Legoupy, G. Dujardiu, R. Dhal, and F. Huct Lett. Org. Chem. 6 2009 359
31. X.Q. Yu, F. Yoshimura, F. Ito, M. Sasaki, A. Hirai, K. Tanino, and M. Miyashita Angew. Chem., Int. Ed. 47 2008 750