Chiral 2-C-methylene glycosides and carbohydrate-derived pyrano[2,3-b][1]benzopyrans: Synthesis via InCl3 catalyzed stereoselective Ferrier rearrangement of 2-C-acetoxymethyl glycal derivatives

Tetrahedron Letters

Volumn 46, Issue 46, 2005, Pages 8047-8051

  Ghosh, Rina ^a   Chakraborty, Arijit ^a   Maiti, Dilip K ^a   Puranik, Vedavati G ^b  

^a JADAVPUR UNIVERSITY   (India)

^b NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

2 C Methylene glycoside; InCl3; Pyranobenzopyran; Stereoselective

Indexed keywords

ALKANOL; BENZOPYRAN DERIVATIVE; CARBOHYDRATE; GLYCOSIDE; INDIUM CHLORIDE; PHENOL;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; FERRIER REARRANGEMENT; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 26844453025     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.059     Document Type: Article

References (38)

1. A. Rosenthal, and M. Sprinzl Can. J. Chem. 48 1970 3253
2. K. Bischofberger, A.J. Brink, O.G. deVilliers, and R.H. Hall J. Chem. Soc., Perkin Trans. 1 1977 1472
3. J. Herscovici, J.M. Egron, and K. Antonakis Carbohydr. Res. 142 1985 324
4. H. Sugimura, K. Osumi, and T. Koyama Chem. Lett. 1991 1379
5. H. Satoh, Y. Yoshimura, M. Watanabe, N. Ashida, and K. Ijichi Nucleosides Nucleotides 17 1998 65
6. V. Samano, and M.J. Robins Synthesis 1991 283
7. M.H. Ali, P.M. Collins, and W.G. Overend Carbohydr. Res. 205 1990 428
8. Y. Chapleur, and F. Chrotien S. Hanessian Preparative Carbohydrate Chemistry 1997 Marcel Dekker NY and references cited therein
9. A. Matsuda, K. Takenuki, M. Tanaka, T. Saski, and T. Ueda J. Med. Chem. 34 1991 812
10. H.C. Baker, J. Banzon, J.M. Bollinger, J. Stubbe, V. Samano, M.J. Robins, B. Lippert, E. Jarvi, and R. Resvick Chemtracts-Org. Chem. 4 1991 426
11. E.D. Rekai, G. Rubinstenn, J.-M. Mallet, and P. Sinäy Synlett 1998 831
12. A.J. Castellino, and H. Rapoport J. Org. Chem. 51 1986 1006
13. K.-i. Tadano, H. Yamada, Y. Idogaki, S. Ogawa, and T. Suami Tetrahedron Lett. 29 1988 655
14. M. del Fernández, B. Esquivel, J. Cárdenas, A.A. Sárchez, R.A. Toscano, and L. Rodriǧuez-Halm Tetrahedron Lett. 47 1991 7199
15. M. Davis, and M. Pettett Aust. J. Chem. 32 1979 369
16. A. Rustaiyan, L. Nazarians, and F. Bohlmann Phytochemistry 19 1980 1254
17. P. Bravo, C. Ticozzi, A.M. Maccioni, and P. Traldi J. Heterocycl. Chem. 24 1987 895
18. L. Diao, C. Yang, and P. Wan J. Am. Chem. Soc. 117 1995 5369
19. H. Miyazaki, K. Honda, M. Asami, and S. Inoue J. Org. Chem. 64 1999 9507
20. H. Miyazaki, Y. Honda, K. Honda, and S. Inoue Tetrahedron Lett. 41 2000 2643
21. D.L. Boger, and S.M. Weinreb Hetero-Diels-Alder Methodology in Organic Synthesis 1987 Academic Press NY Chapter 7, p 167
22. T.R. Kasturi, P.A. Reddy, A.B. Mandal, R. Sivaramakrishnan, B. Rajasekhar, K.B. Ganesha Prasad, R. Radhakrishnan, and M.A. Viswamitra Tetrahedron 46 1990 7047
23. T.R. Kasturi, A.B. Mandal, P.A. Reddy, K.B. Prasad, and B. Rajasekhar Tetrahedron 47 1991 5245
24. C. Booma, and K.K. Balasubramaian J. Chem. Soc., Chem. Commun. 1993 1394
25. C. Booma, and K.K. Balasubramanian Tetrahedron Lett. 34 1993 6757
26. N.G. Ramesh, and K.K. Balasubramanian Eur. J. Org. Chem. 68 2003 4477
27. A. Gupta, and Y.D. Vankar Tetrahedron 56 2000 8525
28. R. Ghosh, D. De, B. Shown, and S.B. Maiti Carbohydr. Res. 321 1999 1
29. R. Ghosh, A. Chakraborty, D. De, and S.B. Maiti Indian J. Chem. 41B 2002 1299
30. R. Ghosh, A. Chakraborty, D.K. Maiti, and S.B. Maiti Indian J. Chem. 41B 2002 583
31. R. Ghosh, A. Chakraborty, and D.K. Maiti Synth. Commun. 33 2003 1623
32. R. Ghosh, A. Chakraborty, and D.K. Maiti Indian J. Chem. 42B 2003 602
33. R. Ghosh, S. Maiti, A. Chakraborty, and D.K. Maiti J. Mol. Catal. A: Chem. 210 2004 53
34. R. Ghosh, S. Maiti, and A. Chakraborty J. Mol. Catal. A: Chem. 215 2004 49
35. R. Ghosh, A. Chakraborty, and S. Maiti Arkivoc xiv 2004 1
36. R. Ghosh, S. Maiti, and A. Chakraborty J. Mol. Catal. A: Chem. 217 2004 47
37. +] 299.1261, found 299.1259.
38. -3.