Concise and divergent approach to 3-O-acyl-l-noviose derivatives and their 3-amino bioisosteres: 3-O-Benzoyl-l-noviose and N-benzoyl-3-amino-l-noviose

Tetrahedron Letters

Volumn 52, Issue 19, 2011, Pages 2450-2453

  Luo, Jisheng ^a   Yu, Xiaoming ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

3 O acyl l Noviose; Aminocoumarin; Bioisostere

Indexed keywords

3 AMINO LEVO NOVIOSE BIOISOSTERE; 3 O BENZOYL LEVO NOVIOSE; ALDEHYDE; AMINOCOUMARIN DERIVATIVE; GUANIDINE; N BENZOYL 3 AMINO LEVO NOVIOSE; PYRAN DERIVATIVE; TARTARIC ACID; UNCLASSIFIED DRUG;

ALLYLATION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; EPOXIDATION;

EID: 79953727922     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.02.092     Document Type: Article

References (32)

1. A. Maxwell Trends Microbiol. 5 1997 102 109
2. M. Oblak, M. Kotnik, and T. Solmajer Curr. Med. Chem. 14 2007 2033 2047
3. L. Heide Nat. Prod. Rep. 26 2009 1241 1250
4. S.M. Li, and L. Heide Curr. Med. Chem. 12 2005 419 427
5. G.S. Bisacchi, and J. Dumas Annu. Rep. Med. Chem. 44 2009 379 396
6. Y. He, J. Xue, Y. Zhou, J. Yang, and X. Yu Tetrahedron Lett. 50 2009 2317 2319
7. S. Hanessian, and L. Auzzas Org. Lett. 10 2008 261 264
8. D.S. Reddy, G. Srinivas, B.M. Rajesh, M. Kannan, T.V. Rajale, and J. Iqbal Tetrahedron Lett. 47 2006 6373 6375
9. X.M. Yu, G. Shen, and B.S.J. Blagg J. Org. Chem. 69 2004 7375 7378
10. M. Jeselnik, I. Leban, S. Polanc, and M. Kocevar Org. Lett. 5 2003 2651 2653
11. D.W. Gammon, R. Hunter, and S. Wilson Tetrahedron Lett. 43 2002 3141 3144
12. M. Takeuchi, T. Taniguchi, and K. Ogasawara Tetrahedron Lett. 41 2000 2609 2611
13. A.-M. Periers, P. Laurin, Y. Benedetti, S. Lachaud, D. Ferroud, A. Iltis, J.-L. Haesslein, M. Klich, G. L'Hermite, and B. Musicki Tetrahedron Lett. 41 2000 867 871
14. P. Laurin, D. Ferroud, L. Schio, M. Klich, C. Dupuis-Hamelin, P. Mauvais, P. Lassaigne, A. Bonnefoy, and B. Musicki Bioorg. Med. Chem. Lett. 9 1999 2875 2880
15. W.M. Pankau, and W. Kreiser Helv. Chim. Acta 81 1998 1997 2004
16. W.M. Pankau, and W. Kreiser Tetrahedron Lett. 39 1998 2089 2090
17. A. Klemer, and M. Waldmann Liebigs Ann. Chem. 1986 221 225
18. J. Kiss, and H. Spiegelberg Helv. Chim. Acta 47 1964 398 407
19. S.H. Olson, and L.H. Slossberg Tetrahedron Lett. 44 2003 61 63
20. C.A. Lipinski Annu. Rep. Med. Chem. 21 1986 283 291
21. J. McNulty, and J. Mao Tetrahedron Lett. 43 2002 3857 3861
22. Y. Tsutomu, S. Kenji, Y. Takehiro, and S. Shiroshi Synlett 1995 847 849
23. A shorter sequence without TBS protection-deprotection was investigated, but the Grignard reaction of dimethyl l-tartrate monomethyl ether gave triol 18 in poor yield due to incomplete conversion.
24. Compound 9 and 19 are easily separable by chromatography on silica gel, and their relative stereochemistry was determined as follow:
25. D.A. Conlon, D. Kumke, C. Moeder, M. Hardiman, G. Hutson, and L. Sailer Adv. Synth. Catal. 346 2004 1307 1315
26. C.-J. Li, and T.H. Chan Tetrahedron Lett. 32 1991 7017 7020
27. C.-J. Li, and T.H. Chan Tetrahedron 55 1999 11149 11176
28. A. D'Alfonso, M. Pasi, A. Porta, G. Zanoni, and G. Vidari Org. Lett. 12 2010 596 599
29. D.W. Norbeck, J.B. Kramer, and P.A. Lartey J. Org. Chem. 52 1987 2174 2179
30. D.A. Cogan, G. Liu, and J. Ellman Tetrahedron 55 1999 8883 8904
31. Relative stereochemistry determined as follow
32. F.A. Davis, and B.-C. Chen Chem. Rev. 92 1992 919 934