An efficient and convenient formal synthesis of Jaspine B from d-xylose

Carbohydrate Research

Volumn 351, Issue , 2012, Pages 126-129

  Zhao, Ming Li ^a   Zhang, En ^a   Gao, Jie ^a   Zhang, Zhao ^a   Zhao, Yu Tao ^a   Qu, Wen ^a   Liu, Hong Min ^a  

^a ZHENGZHOU UNIVERSITY   (China)

Author keywords

d Xylose; Formal synthesis; Jaspine B

Indexed keywords

CONFIGURATION INVERSION; D-XYLOSE; EPOXIDE RING-OPENING REACTION; FORMAL SYNTHESIS; HYDROXYL GROUPS; OXIDATION AND REDUCTION; STEREO-SELECTIVE;

SYNTHESIS (CHEMICAL);

ORGANIC COMPOUNDS;

EPOXIDE; HYDROXYL GROUP; JASPINE B; SPHINGOSINE DERIVATIVE; UNCLASSIFIED DRUG; XYLOSE;

ARTICLE; COLUMN CHROMATOGRAPHY; CRYSTALLIZATION; DRUG PURIFICATION; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; RING OPENING; STEREOCHEMISTRY;

CHEMISTRY TECHNIQUES, SYNTHETIC; CRYSTALLIZATION; SPHINGOSINE; XYLOSE;

EID: 84862776622     PISSN: 00086215     EISSN: 1873426X     Source Type: Journal    
DOI: 10.1016/j.carres.2012.01.013     Document Type: Article

References (50)

1. I. Kuroda, M. Musman, I.I. Ohtani, T. Ichiba, J. Tanaka, D.G. Gravalos, and T. Higa J. Nat. Prod. 65 2002 1505 1506
2. V. Ledroit, C. Debitus, C. Lavaud, and G. Massiot Tetrahedron Lett. 44 2003 225 228
3. D. Canals, D. Mormeneo, G. Fabriàs, A. Llebaria, J. Casas, and A. Delgado Bioorg. Med. Chem. 17 2009 235 241
4. Y. Salma, E. Lafont, N. Therville, S. Carpentier, M.J. Bonnafé, T. Levade, Y. Génisson, and N. Andrieu-Abadie Biochem. Pharmacol. 78 2009 477 485
5. Y. Salma, S. Ballereau, C. Maaliki, S. Ladeira, N. Andrieu-Abadie, and Y. Génisson Org. Biomol. Chem. 8 2010 3227 3243
6. Y. Yoshimitsu, S. Oishi, J. Miyagaki, S. Inuki, H. Ohno, and N. Fujii Bioorg. Med. Chem. 19 2011 5402 5408
7. For a review, see E. Abraham, S.G. Davies, P.M. Roberts, A.J. Russell, and J.E. Thomson Tetrahedron: Asymmetry 19 2008 1027 1047
8. R.J.B.H.N. van den Berg, T.J. Boltje, C.P. Verhagen, R.E.J.N. Litjens, G.A. van der Marel, and H.S. Overkleeft J. Org. Chem. 71 2006 836 839
9. T. Lee, S. Lee, Y.S. Kwak, D. Kim, and S. Kim Org. Lett. 9 2007 429 432
10. K.R. Prasad, and A. Chandrakumar J. Org. Chem. 72 2007 6312 6315
11. Y. Ichikawa, K. Matsunaga, T. Masuda, H. Kotsuki, and K. Nakano Tetrahedron 64 2008 11313 11318
12. G. Reddipalli, M. Venkataiah, M.K. Mishra, and N.W. Fadnavis Tetrahedron: Asymmetry 20 2009 1802 1805
13. K.R. Prasad, and P. Penchalaiah Tetrahedron: Asymmetry 22 2011 1400 1403
14. P. Bhaket, K. Morris, C.S. Stauffer, and A. Datta Org. Lett. 7 2005 875 876
15. P. Vichare, and A. Chattopadhyay Tetrahedron: Asymmetry 21 2010 1983 1987
16. G.S. Rao, N. Sudhakar, B.V. Rao, and S.J. Basha Tetrahedron: Asymmetry 21 2010 1963 1970
17. G.S. Rao, and B.V. Rao Tetrahedron Lett. 52 2011 6076 6079
18. L.V.R. Reddy, P.V. Reddy, and A.K. Shaw Tetrahedron: Asymmetry 18 2007 542 546
19. A. Sánchez-Eleuterio, L. Quintero, and F. Sartillo-Piscil J. Org. Chem. 76 2011 5466 5471
20. G.S. Rao, and B.V. Rao Tetrahedron Lett. 52 2011 4861 4864
21. C. Ribes, E. Falomir, M. Carda, and J.A. Marco Tetrahedron 62 2006 5421 5425
22. Y. Génisson, L. Lamandé, Y. Salma, N. Andrieu-Abadie, C. André, and M. Baltas Tetrahedron: Asymmetry 18 2007 857 864
23. E. Abraham, J.I. Candela-Lena, S.G. Davies, M. Georgiou, R.L. Nicholson, P.M. Roberts, A.J. Russell, E.M. Sánchez-Fernández, A.D. Smith, and J.E. Thomson Tetrahedron: Asymmetry 18 2007 2510 2513
24. T. Yakura, S. Sato, and Y. Yoshimoto Chem. Pharm. Bull. 55 2007 1284 1286
25. K. Venkatesan, and K.V. Srinivasan Tetrahedron: Asymmetry 19 2008 209 215
26. E. Abraham, E.A. Brock, J.I. Candela-Lena, S.G. Davies, M. Georgiou, R.L. Nicholson, J.H. Perkins, P.M. Roberts, A.J. Russell, E.M. Sánchez- Fernández, P.M. Scott, A.D. Smith, and J.E. Thomson Org. Biomol. Chem. 6 2008 1665 1673
27. D. Enders, V. Terteryan, and J. Paleček Synthesis 14 2008 2278 2282
28. H. Urano, M. Enomoto, and S. Kuwahara Biosci. Biotechnol. Biochem. 74 2010 152 157
29. Y. Salma, S. Ballereau, C. Maaliki, S. Ladeira, N. Andrieu-Abadieb, and Y. Génisson Org. Biomol. Chem. 8 2010 3227 3243
30. J. Llaveria, Y. Díaz, M.I. Matheu, and S. Castillón Eur. J. Org. Chem. 2011 1514 1519
31. Y. Salma, S. Ballereau, S. Ladeira, C. Lepetit, R. Chauvin, N. Andrieu-Abadie, and Y. Génisson Tetrahedron 67 2011 4253 4262
32. S. Ballereau, N. Andrieu-Abadie, N. Saffon, and Y. Génisson Tetrahedron 67 2011 2570 2578
33. N. Sudhakar, A.R. Kumar, A. Prabhakar, B. Jagadeesh, and B.V. Rao Tetrahedron Lett. 46 2005 325 327
34. M. Passiniemi, and A.M.P. Koskinen Tetrahedron Lett. 49 2008 980 983
35. S. Inuki, Y. Yoshimitsu, S. Oishi, N. Fujii, and H. Ohno Org. Lett. 11 2009 4478 4481
36. S. Inuki, Y. Yoshimitsu, S. Oishi, N. Fujii, and H. Ohno J. Org. Chem. 75 2010 3831 3842
37. Y. Yoshimitsu, S. Inuki, S. Oishi, N. Fujii, and H. Ohno J. Org. Chem. 75 2010 3843 3846
38. M. Passiniemi, and A.M.P. Koskinen Org. Biomol. Chem. 9 2011 1774 1783
39. S. Chandrasekhar, B. Tiwari, and S.J. Prakash ARKIVOC 2006 155 161
40. C.V. Ramana, A.G. Giri, S.B. Suryawanshi, and R.G. Gonnade Tetrahedron Lett. 48 2007 265 268
41. G. Jayachitra, N. Sudhakar, R.K. Anchoori, B.V. Rao, S. Roy, and R. Banerjeeb Synthesis 1 2010 115 119
42. S. Cruz-Gregorio, E. Espinoza-Rojas, L. Quintero, and F. Sartillo-Piscil Tetrahedron Lett. 52 2011 6370 6371
43. Y. Du, J. Liu, and R.J. Linhardt J. Org. Chem. 71 2006 1251 1253
44. J. Liu, Y. Du, X. Dong, S. Meng, J. Xiao, and L. Cheng Carbohydr. Res. 341 2006 2653 2657
45. H.M. Liu, D.P. Zou, F.Y. Zhang, W.G. Zhu, and T. Peng Eur. J. Org. Chem. 10 2004 2103 2106
46. D.P. Zou, S.X. Cao, W.C. Xu, and H.M. Liu Carbohydr. Res. 340 2005 2411 2421
47. X.M. Ji, J. Mo, H.M. Liu, and H.P. Sun Carbohydr. Res. 341 2006 2312 2320
48. R.R. Talekar, and R.H. Wightman Tetrahedron 53 1997 3831 3842
49. H.W. Yu, H.Y. Zhang, Z.J. Yang, J.M. Min, L.T. Ma, and L.H. Zhang Pure Appl. Chem. 70 1998 435 438
50. J. Moravcová, J. Čapková, and J. Staněk Carbohydr. Res. 263 1994 61 66