Preparation of peptide-like bicyclic lactams via a sequential Ugi reaction - Olefin metathesis approach

Tetrahedron Letters

Volumn 45, Issue 31, 2004, Pages 5987-5990

  Krelaus, Ralf ^a   Westermann, Bernhard ^a  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

Author keywords

Isocyanide; Olefin metathesis; Peptide mimic; Ugi reaction

Indexed keywords

LACTAM DERIVATIVE; PEPTIDE;

ADDITION REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CONFORMATION; RING CLOSING METATHESIS; UGI MULTICOMPONENT REACTION;

EID: 3142683044     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.06.052     Document Type: Article

References (17)

1. The work has been carried out mainly at the University of Paderborn, Germany. It has been presented, in part, at the Chemiedozententagung, abstract A33, Cologne, Germany, 2002
2. Dömling A., Ugi I. Angew. Chem., Int. Ed. 39:2000;3168-3210
3. Harriman G.C.B. Tetrahedron Lett. 38:1997;5591-5594
4. Short K.M., Mjalli M.M. Tetrahedron Lett. 38:1997;359-362
5. Hanusch-Kompa C., Ugi I. Tetrahedron Lett. 39:1998;2725-2728
6. Marcaccini S., Pepino R., Torroba T., Miguel D., Garcia-Valverde M. Tetrahedron Lett. 43:2002;8591-8593
7. Zimmer R., Ziemer A., Gruner M., Brüdgam I., Hartl H., Reissig H.U. Synthesis. 2001;1649-1658
8. Westermann, B.; Diedrichs, N.; Krelaus, R.; Walter, A.; Gedrath, I. Tetrahedron Lett., see preceding paper, doi:10.1016/j.tetlet.2004.06.051
9. Diedrichs N., Westermann B. Synlett. 1999;1127-1129
10. Diedrichs N., Krelaus R., Gedrath I., Westermann B. Can. J. Chem. 80:2002;686-691
11. Lee D., Sello J.K., Schreiber S.L. Org. Lett. 2:2000;709-712
12. Hebach C., Kazmaier U. Chem. Commun. 2003;596-597
13. Beck B., Larbig G., Magnin-Lachaux M., Picard A., Herdtweck E., Dömling A. Org. Lett. 5:2003;1047-1050
14. General procedure for the synthesis of lactam 13: levulinic acid 1 (1.00 g, 8.6 mmol) was dissolved in dry methanol (43 mL) and isobutylamine 3 (0.79 g, 10.8 mmol) was added. The mixture was stirred for 30 min at room temperature to allow formation of the imine. 1-Isocyanobutane 8 (0.71 g, 8.6 mmol) was added and the mixture is stirred for two days at room temperature.
15. Orru, R., personal communication
16. Ma S., Ni B. Org. Lett. 4:2002;639-641
17. (b) Ma, S.; Ni, B. Chem. Eur. J. 2004, online preprint