A novel building block for the synthesis of isofagomin analogues

Tetrahedron Asymmetry

Volumn 9, Issue 9, 1998, Pages 1519-1524

  Altenbach, Hans Josef ^a   Blanda, Gaetano ^a  

^a UNIVERSITY OF WUPPERTAL   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

3 ACETOXYMETHYL 3,6 DIHYDRO 2H PYRIDINE 1 CARBOXYLATE; 3 BUTYRYL OXYMETHYL 3,6 DIHYDRO 2H PYRIDINE 1 CARBOXYLIC ACID PHENYL ESTER; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; ISOFAGOMIN; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; BURKHOLDERIA CEPACIA; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; ESTERIFICATION; PRIORITY JOURNAL; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0032496130     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(98)00090-1     Document Type: Article

References (37)

1. (a) Le Merrer, Y.; Poitout, L.; Depezay, J.-C.; Dosbaa, I.; Geoffroy, S.; Foglietti, M.-J. Bioorg. Med. Chem. 1997, 5, 519.
2. (b) Huwe, C. M.; Blechert, S. Synthesis 1997, 61.
3. (c) Johns, B. A.; Pan, Y. T.; Elbein, A. D.; Johnson, C. R. J. Am. Chem. Soc. 1997, 119, 4856.
4. (d) Carretero, J. C.; Arrayas, R. G.; Storch de Gracia, I. Tetrahedron Lett. 1997, 38, 8537.
5. (e) Brandstetter, T. W.; Davis, B.; Hyett, D.; Smith, C.; Hackett, L.; Winchester, B. W.; Fleet, G. W. J. Tetrahedron Lett. 1995, 36, 7511.
6. (f) Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182.
7. (a) Winchester, B.; Fleet, G. W. Glycobiology 1992, 2, 199, and references cited therein.
8. (b) Kausal, G. P.; Elbein, A. D. Trends Gycosci. Glycotechnol. 1993, 5, 209.
9. (c) Sinnott, M. L Chem. Rev. 1990, 90, 1171.
10. Tsuruoka, T.; Fukuyasu, H.; Ishii, M.; Usui, T.; Shibahara, S.; Inouye, S. J. Antibiotics 1996, 9, 155.
11. Fleet, G. W. J.; Karpas, A.; Dwek, R. A.; Fellows, L. E.; Tyms, A. S.; Petrrsson, S.; Namgoong, S. K.; Ramsden, N. G.; Smith, P. W.; Chan Son, J.; Wilson, F.; Witty, D. R.; Jacob, G. S.; Rademacher, T. W.; FEBS Lett. 1988, 237, 128.
12. (a) Jerpersen, T. M.; Dong, W.; Sierks, M. R.; Skrydstrup, T.; Lundt, I.; Bols, M. Angew. Chem. 1994, 106, 1858.
13. (b) Ichikawa, M.; Ichikawa, Y. Tetrahedron Lett. 1995, 36, 4585.
14. (a) Ref. 5.
15. (b) Jerspersen, T. M.; Bols, M.; Sierks, M. R.; Skrydstrup, M. R. Tetrahedron 1994, 50, 13449.
16. (c) Bols, M. Tetrahedron Lett. 1996, 37, 2097.
17. (d) Hansen, A.; Tagmose, T. M.; Bols, M. Chem. Commun. 1996, 2649.
18. (e) Jerpersen, T.; Dong, W.; Sierks, M. R.; Skrydstrup, T.; Bols, M. Biochemistry 1996, 35, 2788.
19. (f) Hansen, A.; Tagmose, T. M.; Bols, M. Tetrahedron 1997, 53, 697.
20. (g) Ichikawa, M.; Ichikawa, Y. Bioorg. Med. Chem. 1995, 3, 161.
21. Treves, G.; Baum, B.; Burton, M. (FMC Corp.), U.S. patent 4467095 A, 1984 [Chem. Abstr. 1984, 101, 211000s].
22. (a) Allan, R. D.; Fong, J. Aust. J. Chem. 1983, 36, 601.
23. (b) Müller-Uri, C.; Singer, E. A.; Fleischhacker, W. J. Med. Chem. 1986, 29, 125.
24. (c) Clinch, K.; Marquez, C. J.; Parrott, M. J.; Ramage, R. Tetrahedron 1989, 45, 239.
25. Bunnell, C. A.; Fuchs, P. L. J. Am. Chem. Soc. 1977, 99, 5184.
26. (a) Wright, W. B.; Brabander, H. J. J. Org. Chem. 1961, 26, 4057.
27. (b) Oediger, H.; Joop, N. Liebigs Ann. Chem. 1972, 764, 21.
28. However, there are many examples of enzyme catalysed enantiotopos-differentiating acylation of prochiral primary diols or of enzyme catalysed enantiotopos-differentiating hydrolysis of prochiral primary diol diacetates. See: (a) Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis, VCH, Weinheim; 1995. (b) Weissfloch, A. N. E.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 6959.
29. However, there are many examples of enzyme catalysed enantiotopos-differentiating acylation of prochiral primary diols or of enzyme catalysed enantiotopos-differentiating hydrolysis of prochiral primary diol diacetates. See: (a) Drauz, K.; Waldmann, H. Enzyme Catalysis in Organic Synthesis, VCH, Weinheim; 1995. (b) Weissfloch, A. N. E.; Kazlauskas, R. J. J. Org. Chem. 1995, 60, 6959.
30. Wirtz, B.; Walther, W. Tetrahedron: Asymmetry 1992, 3, 1049.
31. For successful enzymatic resolutions in related 5-membered systems see: (a) Altenbach, H.-J.; Merhof, G. F.; Brauer, D. J. Tetrahedron: Asymmetry 1996, 7, 2493. (b) Schieweck, F.; Altenbach, H.-J. Tetrahedron: Asymmetry 1998, 9, 403.
32. For successful enzymatic resolutions in related 5-membered systems see: (a) Altenbach, H.-J.; Merhof, G. F.; Brauer, D. J. Tetrahedron: Asymmetry 1996, 7, 2493. (b) Schieweck, F.; Altenbach, H.-J. Tetrahedron: Asymmetry 1998, 9, 403.
33. Screening with enzymes from Candida antartica (Novozym 435), Candida cylindracae (Sigma), Candida cylindracae (Meito MY), Pseudomonas caepacia Amano PS), Pseudomonas fluorescens (Fluka), Aspergillus oryzae (Lipozym IM), Pseudomonas species (Amano AK), Alcaligens species (Meito PL), Acromobacter species (Meito AL), pig pancreas lipase (Type II, Aldrich) and pig liver esterase.
34. 2). HPLC: Chiracel OD-column (DAICEL Chemical Industry); heptane:ispropanol=90:10.
35. Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Shih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
36. 2). HPLC: Chiracel OD-column (DAICEL Chemical Industry); heptane:ispropanol=90:10.
37. Bettoni, G.; Duranti, E.; Tortorella, V. Gazz. Chim. Ital. 1972, 102, 189.