Synthesis of 4-maleimidobutyric acid and related maleimides

Synthesis

Volumn , Issue 8, 2008, Pages 1316-1318

  De Figueiredo, Renata Marcia ^a   Oczipka, Philipp ^a   Fröhlich, Roland ^b   Christmann, Mathias ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Aminobutanoic acid; Condensations; Cross linking reagents; Imides; Maleic anhydride

Indexed keywords

CONDENSATION; CROSSLINKING; DERIVATIVES; ESTERS; MALEIC ANHYDRIDE; SYNTHESIS (CHEMICAL);

AMINOBUTANOIC ACID; CROSS-LINKING REAGENTS; IMIDES;

ORGANIC ACIDS;

3 (2,5 DIOXO 2,5 DIHYDRO 1H PYRROL 1 YL)PROPANOIC ACID; 4 (2,5 DIOXO 2,5 DIHYDRO 1H PYRROL 1 YL)BUTANOIC ACID; 4 (3 METHYL 2,5 DIOXO 2,5 DIHYDRO 1H PYRROL 1 YL)BUTANOIC ACID; 4 MALEIMIDOBUTYRIC ACID; 5 (2,5 DIOXO 2,5 DIHYDRO 1H PYRROL 1 YL)PENTANOIC ACID; 6 (2,5 DIOXO 2,5 DIHYDRO 1H PYRROL 1 YL)HEXANOIC ACID; 6 (3 METHYL 2,5 DIOXO 2,5 DIHYDRO 1H PYRROL 1 YL)HEXANOIC ACID; BUTYRIC ACID; BUTYRIC ACID DERIVATIVE; CROSS LINKING REAGENT; HEXANOIC ACID DERIVATIVE; MALEIMIDE; PROPIONIC ACID DERIVATIVE; PYRROLIZIDINE; TELOMERASE INHIBITOR; UCS1025A; VALERIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ENANTIOSELECTIVITY; SYNTHESIS;

EID: 43049090159     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032016     Document Type: Article

References (16)

1. Rich, D. H.; Gesellchen, P. D.; Tong, A.; Cheung, A.; Buckner, C. K. J. Med. Chem. 1975, 18, 1004.
2. (a) Stuhlmann, F.; Jäschke, A. J. Am. Chem. Soc. 2002, 124, 3238.
3. (b) Herrmann, A.; Mihov, G.; Vandermeulen, G. W. M.; Klok, H.-A.; Müllen, K. Tetrahedron 2003, 59, 3925.
4. (c) Bennes, R. M.; Philp, D. Org. Lett. 2006, 8, 3651.
5. (d) de Araújo, A. D.; Palomo, J. M.; Cramer, J.; Seitz, O.; Alexandrov, K.; Waldmann, H. Chem. Eur. J. 2006, 12, 6095.
6. (e) Meyer-Losic, F.; Quinonero, J.; Dubois, V.; Alluis, B.; Dechambre, M.; Michel, M.; Cailler, F.; Fernandez, A.-M.; Trauet, A.; Kearsey, J. J. Med. Chem. 2006, 49, 6908.
7. Lambert, T. H.; Danishefsky, S. J. J. Am. Chem. Soc. 2006, 128, 426.
8. Hoye, T. R.; Dvornikovs, V. J. Am. Chem. Soc. 2006, 128, 2550.
9. (a)Nakai, R.; Ogawa, H.; Asai, A.; Ando, K.; Agatsuma, T.; Matsumiya, S.; Akinaga, S.; Yamashita, Y.; Mizukami, T. J. Antibiot. 2000, 53, 294.
10. (b) Agatsuma, T.; Akama, T.; Nara, S.; Matsumiya, S.; Nakai, R.; Ogawa, H.; Otaki, S.; Ikeda, S.-i.; Saitoh, Y.; Kanda, Y. Org. Lett. 2002, 4, 4387.
11. (c) Nakai, R.; Ishida, H.; Asai, A.; Ogawa, H.; Yamamoto, Y.; Kawasaki, H.; Akinaga, S.; Mizukami, T.; Yamashita, Y. Chem. Biol. 2006, 13, 183.
12. (a) de Figueiredo, R. M.; Fröhlich, R.; Christmann, M. Angew. Chem. Int. Ed. 2007, 46, 2883.
13. (b) de Figueiredo, R. M.; Voith, M.; Fröhlich, R.; Christmann, M. Synlett 2007, 391.
14. (a) Mantovani, G.; Lecolley, F.; Tao, L.; Haddleton, D. M.; Clerx, J.; Cornelissen, J. J. L. M.; Velonia, K. J. Am. Chem. Soc. 2005, 127, 2966.
15. (b) Lavis, L. D.; Chao, T.; Raines, R. T. ACS Chem. Biol. 2006, 1, 252.
16. CCDC 651593 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/ retrieving.html [or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK, fax: +44(1223)336033, E-mail: deposit@ccdc.cam.ac. uk.