Convenient one-pot synthesis of thiosugars and their efficient conversion to polyoxygenated cycloalkenes

Tetrahedron

Volumn 68, Issue 22, 2012, Pages 4242-4247

  Zhang, Jingjing ^a   Niu, Youhong ^a,b   Cao, Xiaoping ^b   Ye, Xin Shan ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b LANZHOU UNIVERSITY   (China)

Author keywords

Cycloalkenes; Ramberg Backlund reaction; Tetrahydrothiopyrans; Thiepanes; Thiosugars

Indexed keywords

ALDITOL; CYCLOALKENE; THIOPYRAN DERIVATIVE; THIOSUGAR;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; ONE POT SYNTHESIS; OXYGENATION; PRIORITY JOURNAL; PROCESS DEVELOPMENT; REACTION ANALYSIS;

EID: 84860467490     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2012.03.086     Document Type: Article

References (53)

1. H. Yuasa, Y. Izukawa, and H. Hashimoto Curr. Top. Med. Chem. 9 2009 76 86
2. H. Yuasa, Y. Nakano, and H. Hashimoto Carbohydr. Lett. 2 1996 23 26
3. T. Kajimoto, K.K.-C. Liu, R.L. Pederson, Z. Zhong, Y. Ichikawa, J.A. Porco Jr., and C.-H. Wong J. Am. Chem. Soc. 113 1991 6187 6196
4. Y. Yoshimura, M. Endo, and S. Sakata Tetrahedron Lett. 40 1999 1937 1940
5. S. Miura, Y. Yoshimura, M. Endo, H. Machida, A. Matsuda, M. Tanaka, and T. Sasaki Cancer Lett. 129 1998 103 110
6. T. Hudlicky, J.D. Price, F. Rulin, and T. Tsunoda J. Am. Chem. Soc. 112 1990 9439 9440
7. R.F. Schinazi, C.K. Chu, A. Peck, A. McMillan, R. Mathis, D. Cannon, L.S. Jeong, J.W. Beach, W.B. Choi, and S. Yeola Antimicrob. Agents Chemother. 36 1992 672 676
8. J.A. Coates, N. Cammack, H.J. Jenkinson, A.J. Jowett, M.I. Jowett, B.A. Pearson, C.R. Penn, P.L. Rouse, K.C. Viner, and J.M. Cameron Antimicrob. Agents Chemother. 36 1992 733 739
9. J.W. Beach, L.S. Jeong, A.J. Alves, D. Pohl, H.O. Kim, C.N. Chang, S.L. Doong, R.F. Schinazi, Y.C. Cheng, and C.K. Chu J. Org. Chem. 57 1992 2217 2219
10. E. Bozo, S. Boros, and J. nos Kuszmann Carbohydr. Res. 311 1998 191 202
11. E. Bozo, T. Gáti, A. Demeter, and J. Kuszmann Carbohydr. Res. 337 2002 1351 1365
12. I. Robina, P. Vogel, and Z.J. Witczak Curr. Org. Chem. 5 2001 1177 1214
13. I. Robina, and P. Vogel Curr. Org. Chem. 6 2002 471 491
14. Y.L. Merrer, M. Fuzier, I. Dosbaa, M.J. Foglietti, and J.C. Depezay Tetrahedron 53 1997 16731 16746
15. V. Cere, G. Mantovani, F. Peri, S. Pollicino, and A. Ricci Tetrahedron 56 2000 1225 1231
16. H.J. Altenbach, and G.F. Merhof Tetrahedron: Asymmetry 7 1996 3087 3090
17. M. Benazza, S. Halila, C. Viot, A. Danquigny, C. Pierru, and G. Demailly Tetrahedron 60 2004 2889 2895
18. M. Fuzier, Y.L. Merrer, and J.C. Depezay Tetrahedron Lett. 36 1995 6443 6446
19. P. Passacantilli, C. Centore, E. Ciliberti, G. Piancatelli, and F. Leonelli Eur. J. Org. Chem. 2006 3097 3104
20. S. Halila, M. Benazza, and G. Demailly Tetrahedron Lett. 42 2001 3307 3310
21. V. Glacon, M. Benazza, D. Beaupere, and G. Demailly Tetrahedron Lett. 41 2000 5053 5056
22. S. Halila, M. Benazza, and G. Demailly Tetrahedron Lett. 43 2002 815 818
23. G.-N. Wang, Y. Xiong, J. Ye, L.-H. Zhang, and X.-S. Ye ACS Med. Chem. Lett. 2 2011 682 686
24. G.-L. Zhang, L.-H. Zhang, and X.-S. Ye Org. Biomol. Chem. 8 2010 5062 5068
25. L.-J. Pang, D. Wang, J. Zhou, L.-H. Zhang, and X.-S. Ye Org. Biomol. Chem. 7 2009 4252 4266
26. G.-N. Wang, G. Reinkensmeier, S. Zhang, J. Zhou, L. Zhang, L.-H. Zhang, T.D. Butters, and X.-S. Ye J. Med. Chem. 52 2009 3146 3149
27. J. Zhou, Y.M. Zhang, X. Zhou, J. Zhou, L.-H. Zhang, X.-S. Ye, and X.-L. Zhang Bioorg. Med. Chem. 16 2008 1605 1612
28. L. Zhang, F. Sun, Y. Li, X. Sun, X. Liu, Y. Huang, L.-H. Zhang, X.-S. Ye, and J. Xiao ChemMedChem 2 2007 1594 1597
29. X.-S. Ye, F. Sun, M. Liu, Q. Li, Y.H. Wang, G.S. Zhang, L.-H. Zhang, and X.-L. Zhang J. Med. Chem. 48 2005 3688 3691
30. M. Violante de Paz Banez, J.A.A. Moreno, and J.A. Galbis J. Carbohydr. Chem. 27 2008 120 140
31. J.K. Gallos, T.V. Koftis, V.I. Karamitrou, and A.E. Koumbis J. Chem. Soc., Perkin Trans. 1 1997 2461 2462
32. Y.H. Jiang, Z.J. Fang, Q.G. Zheng, H.L. Jia, J. Cheng, and B.H. Zheng Synthesis 16 2009 2756 2760
33. Y. Tsuda, T. Nunozawa, and K. Yoshimoto Chem. Pharm. Bull. 28 1980 3223 3231
34. C.G. Mabiala-Bassiloua, M. Zwolinska, H. Therisod, J. Sygusch, and M. Therisod Bioorg. Med. Chem. Lett. 18 2008 1735 1737
35. L. Ackermann, D.E. Tom, and A. Furstner Tetrahedron 56 2000 2195 2202
36. M.-C. Matos, and P.V. Murphy J. Org. Chem. 72 2007 1803 1806
37. A. Arcelli, V. Cerè, F. Peri, S. Pollicino, and A. Ricci Tetrahedron: Asymmetry 13 2002 191 196
38. C.U. Kim, L.R. McGee, S.H. Krawczyk, E. Harwood, Y. Harada, S. Swaminathan, N. Bischofberger, M.S. Chen, J.M. Cherrington, S.F. Xiong, L. Griffin, K.C. Cundy, A. Lee, B. Yu, S. Gulnik, and J.W. Erickson J. Med. Chem. 39 1996 3431 3434
39. M. Suzuki, A. Yanagisawa, and R. Noyori J. Am. Chem. Soc. 110 1988 4718 4726
40. T. Aoyagi, T. Yamamoto, K. Kojiri, H. Morishima, M. Nagai, M. Hamada, T. Takeuchi, and H. Umezawa J. Antibiot. 42 1989 883 889
41. S.B. King, and B. Ganem J. Am. Chem. Soc. 113 1991 5089 5090
42. C. Li, and P.L. Fuchs Tetrahedron Lett. 35 1994 5121 5124
43. B.M. Trost, and D.L. Van Vranken J. Am. Chem. Soc. 113 1991 6317 6318
44. B.M. Trost, and D.L. Van Vranken J. Am. Chem. Soc. 115 1993 444 458
45. B.M. Trost Pure Appl. Chem. 64 1992 315 322
46. S.I. de Gracia, H. Dietrich, S. Bobo, and J.L. Chiara J. Org. Chem. 63 1998 5883 5889
47. M. Seepersaud, and Y. Al-Abed Tetrahedron Lett. 41 2000 4291 4293
48. J.E. McMurry Chem. Rev. 89 1989 1513 1524
49. M. Ephritikhine Chem. Commun. 1998 2549 2554
50. B.R. Galan, K.P. Kalbarczyk, S. Szczepankiewicz, J.B. Keister, and S.T. Diver Org. Lett. 9 2007 1203 1206
51. L. Ramberg, and B. Backlund Ark. Kemi. Mineral. Geol. 27 1940 1 50
52. M.G. Szczepina, B.D. Johnston, Y. Yuan, B. Svensson, and B.M. Pinto J. Am. Chem. Soc. 126 2004 12458 12469
53. L.A. Agrofoglio, F. Amblard, S.P. Nolan, S. Charamon, I. Gillaizeau, T.A. Zevaco, and P. Guenot Tetrahedron 60 2004 8397 8404