Synthesis of congeners of migrastatin and dorrigocin A from d-xylose

Tetrahedron Letters

Volumn 51, Issue 40, 2010, Pages 5262-5264

  Zhou, Ying ^b   Murphy, Paul V ^a  

^a NATIONAL UNIVERSITY OF IRELAND   (Ireland)

^b NONE

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALKENE; ALKENE DERIVATIVE; ANTINEOPLASTIC AGENT; DORRIGOCIN A; DRUG ANALOG; LACTAM DERIVATIVE; LACTONE DERIVATIVE; MACROLACTAM; MACROLACTONE; MIGRASTATIN; UNCLASSIFIED DRUG; XYLOSE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; OLEFINATION; SUBSTITUTION REACTION; WITTIG REACTION;

EID: 77956328979     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.141     Document Type: Article

References (30)

1. N. Nakae, Y. Yoshimoto, M. Ueda, T. Sawa, Y. Takahashi, H. Naganawa, T. Takeuchi, and M.J. Imoto J. Antibiot. 53 2000 1228 1230
2. E.J. Woo, C.M. Starks, J.R. Carney, R. Arslanian, L. Cadapan, S. Zavala, and P. Licari J. Antibiot. 55 2002 141 146
3. J. Ju, S.-K. Lim, H. Jiang, and B. Shen J. Am. Chem. Soc. 127 2005 1622 1623
4. Y. Kloog, and A.D. Cox Mol. Med. Today 6 2000 398 402
5. S. Kadam, and J.B. McAlpine J. Antibiot. 47 1994 875 880
6. C. Gaul, J.T. Njardarson, D. Shan, D.C. Dorn, K.-D. Wu, W.P. Tong, X.-Y. Huang, M.A.S. Moore, and S.J. Danishefsky J. Am. Chem. Soc. 126 2004 11326 11337
7. J.T. Njardarson, C. Gaul, D. Shan, X.-Y. Huang, and S.J. Danishefsky J. Am. Chem. Soc. 126 2004 1038 1040
8. D. Shan, L. Chen, J.T. Njardarson, C. Gaul, X. Ma, S.J. Danishefsky, and X.-Z. Huang Proc. Nat. Acad. Sci. U.S.A. 102 2005 3772 3776
9. T. Oskarsson, P. Nagorny, I.J. Krauss, L. Perez, M. Mandal, G. Yang, O. Ouerfelli, D. Xiao, M.A.S. Moore, M. Massagu, and S.J. Danishefsky J. Am. Chem. Soc. 132 2010 3224 3228
10. G. Anquetin, S.L. Rawe, K. McMahon, E.P. Murphy, and P.V. Murphy Chem. Eur. J. 14 2008 1592 1600
11. G. Anquetin, G. Horgan, S.L. Rawe, D. Murray, A. Madden, P. McMathuna, P. Doran, and P.V. Murphy Eur. J. Org. Chem. 2008 1953 1958
12. J. Ju, S.R. Rajski, S.-K. Lim, J.-W. Seo, N.R. Peters, F.M. Hoffmann, and B. Shen J. Am. Chem. Soc. 131 2009 1370 1371
13. L. Chen, S. Yang, J. Jakoncic, J. Jillian Zhang, and X.-Z. Huang Nature 464 2010 1062 1066
14. For a recent review, see: S. Reymond, and J. Cossy C. R. Chim. 11 2008 1447 1462
15. K. Ando J. Org. Chem. 63 1998 8411 8416
16. K. Ando J. Org. Chem. 65 2000 4745 4749
17. J.R. Dunetz, and W.R. Roush Org. Lett. 10 2008 2059 2062
18. Y. Hayashi, H. Yamaguchi, M. Toyoshima, K. Okado, T. Toyo, and M. Shoji Org. Lett. 10 2008 1405 1408
19. For a recent application of d-xylose as a starting material in natural product synthesis, see: Q. Chen, and Y. Du Tetrahedron Lett. 47 2006 8489 8492
20. Y. Du, Q. Chen, and R.J. Linhardt J. Org. Chem. 71 2006 8446 8451
21. R.E. Ireland, and D.W. Norbeck J. Am. Chem. Soc. 107 1985 3279 3285
22. R. Gigg, and C.D. Warren Journal. Chem. Soc. C 1968 1903 1911
23. -: 283.1545. Found: 283.1556.
24. 1H NMR spectroscopy.
25. S.T. Nguyen, T.M. Trnka, and R.H. Grubbs Acc. Chem. Res. 34 2001 18 29
26. 4,5 and S. Reymond, and J. Cossy Tetrahedron 63 2007 5918 5929
27. Y. Kaburagi, and Y. Kishi Org. Lett. 9 2007 723 726
28. +: 325.1627. Found: 325.1613.
29. J.L. Brazidec, C.L. Gilson III, and M.F. Boehm J. Org. Chem. 70 2005 8212 8215
30. A.K. Chatterjee, T.L. Choi, D.P. Sanders, and R.H. Grubbs J. Am. Chem. Soc. 125 2003 11360 11370