Short and efficient synthesis of diazabicycloalkane dipeptide mimics

Synlett

Volumn , Issue 11, 2002, Pages 1795-1798

  Maison, Wolfgang ^a   Küntzer, Daniela ^a   Grohs, Daniel ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Diels Alder reactions; Dihydroxylations; Heterocycles; Peptide mimics; Peptides

Indexed keywords

CYCLOALKANE DERIVATIVE; DIPEPTIDE;

AMINO ACID ANALYSIS; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; DEGRADATION; DIELS ALDER REACTION; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE; OXIDATION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0036431575     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34901     Document Type: Article

References (29)

1. Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244; Angew. Chem. 1993, 105, 1303.
2. Giannis, A.; Kolter, T. Angew. Chem., Int. Ed. Engl. 1993, 32, 1244; Angew. Chem. 1993, 105, 1303.
3. (a) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699; Angew. Chem. 1994, 106, 1780.
4. (a) Gante, J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1699; Angew. Chem. 1994, 106, 1780.
5. (b) Hruby, V. J.; Li, G.; Haskell-Luevano, C.; Shenderovich, M. Biopolymers 1997, 43, 219.
6. (a) Hanessian, S.; McNaughton-Smith, G.; Lombart, H.-G.; Lubell, W. D. Tetrahedron 1997, 53, 12789.
7. (b) Halab, L.; Gosselin, F.; Lubell, W. D. Biopolymers 2000, 55, 101.
8. Recent examples include: (a) Polyak, F.; Lubell, W. D. J. Org. Chem. 2001, 66, 1171. (b) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660. (c) Belvisi, L.; Colombo, L.; Colombo, M.; Di Giacomo, M.; Manzoni, L.; Vodopivec, B.; Scolastico, C. Tetrahedron 2001, 57, 6463. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571. (e) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (f) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087.
9. Recent examples include: (a) Polyak, F.; Lubell, W. D. J. Org. Chem. 2001, 66, 1171. (b) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660. (c) Belvisi, L.; Colombo, L.; Colombo, M.; Di Giacomo, M.; Manzoni, L.; Vodopivec, B.; Scolastico, C. Tetrahedron 2001, 57, 6463. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571. (e) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (f) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087.
10. Recent examples include: (a) Polyak, F.; Lubell, W. D. J. Org. Chem. 2001, 66, 1171. (b) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660. (c) Belvisi, L.; Colombo, L.; Colombo, M.; Di Giacomo, M.; Manzoni, L.; Vodopivec, B.; Scolastico, C. Tetrahedron 2001, 57, 6463. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571. (e) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (f) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087.
11. Recent examples include: (a) Polyak, F.; Lubell, W. D. J. Org. Chem. 2001, 66, 1171. (b) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660. (c) Belvisi, L.; Colombo, L.; Colombo, M.; Di Giacomo, M.; Manzoni, L.; Vodopivec, B.; Scolastico, C. Tetrahedron 2001, 57, 6463. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571. (e) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (f) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087.
12. Recent examples include: (a) Polyak, F.; Lubell, W. D. J. Org. Chem. 2001, 66, 1171. (b) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660. (c) Belvisi, L.; Colombo, L.; Colombo, M.; Di Giacomo, M.; Manzoni, L.; Vodopivec, B.; Scolastico, C. Tetrahedron 2001, 57, 6463. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571. (e) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (f) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087.
13. Recent examples include: (a) Polyak, F.; Lubell, W. D. J. Org. Chem. 2001, 66, 1171. (b) Grossmith, C. E.; Senia, F.; Wagner, J. Synlett 1999, 1660. (c) Belvisi, L.; Colombo, L.; Colombo, M.; Di Giacomo, M.; Manzoni, L.; Vodopivec, B.; Scolastico, C. Tetrahedron 2001, 57, 6463. (d) Angiolini, M.; Araneo, S.; Belvisi, L.; Cesarotti, E.; Checchia, A.; Crippa, L.; Manzoni, L.; Scolastico, C. Eur. J. Org. Chem. 2000, 2571. (e) Sun, H.; Moeller, K. D. Org. Lett. 2002, 4, 1547. (f) Millet, R.; Domarkas, J.; Rombaux, P.; Rigo, B.; Houssin, R.; Hénichart, J.-P. Tetrahedron Lett. 2002, 43, 5087.
14. (a) Tong, Y.; Fobian, Y. M.; Wu, M.; Boyd, N. D.; Moeller, K. D. J. Org. Chem. 2000, 65, 2484.
15. (b) St-Denis, Y.; Augelli-Szafran, C. E.; Bachand, B.; Berryman, K. A.; DiMaio, J.; Doherty, A. M.; Edmunds, J. J.; Leblond, L.; Lévesque, S.; Narasimhan, L. S.; Penvose-Yi, J. R.; Rubin, J. R.; Tarazi, M.; Winocour, P. D.; Siddiqui, M. A. Bioorg. Med. Chem. Lett. 1998, 8, 3193.
16. (c) Fai Chan, M.; Raju, B. G.; Kois, A.; Varughese, J. I.; Varughese, K. I.; Balaji, V. N. Heterocycles 1999, 51, 5.
17. Schally, A. V.; Nagy, A. Eur. J. Endocrinol. 1999, 141, 1.
18. Zaheer, A.; Lenkinski, R. E.; Mahmood, A.; Jones, A. G.; Cantley, L. C.; Frangioni, J. V. Nature Biotech. 2001, 19, 1148.
19. (a) Liu, S.; Edwards, D. S. Chem. Rev. 1999, 99, 2235.
20. (b) Mahmood, A.; Kuchma, M. H.; Goldstone, J.; Morse, C.; Davison, A.; Jones, A. G. In Technetium, Rhenium and other Metals in Chemistry and Nuclear Medicine, Vol. 5; Nicolini M., Mazzi U., Servizi Grafici Editoriali: Padova, 1999, 523.
21. (a) Speckamp, W. N.; Moolenaar, M. J. Tetrahedron 2000, 56, 3817.
22. (b) Thaning, M.; Wistrand, L.-G. Acta Chim. Scand. 1992, 46, 194.
23. (c) Ludwig, C.; Wistrand, L.-G. Acta Chim. Scand. 1994, 48, 367.
24. (d) Maison, W.; Acre, E.; Renold, P.; Kennedy, R.; Kemp, D. S. J. Am. Chem. Soc. 2001, 123, 10245.
25. Maison, W.; Adiwidjaja, G. Tetrahedron Lett. 2002, 43, 5957.
26. Portevin, B.; Benoist, A.; Rémond, G.; Hérve, Y.; Vincent, M.; Lepagnol, J.; De Nanteuil, G. J. Med. Chem. 1996, 39, 2379.
27. (a) Stella, L.; Abraham, H. Tetrahedron 1992, 48, 9707.
28. (b) For an improved large scale protocol see: Ekegren, J. K.; Modin, S. A.; Alonso, D. A.; Andersson, P. G. Tetrahedron: Asymmetry 2002, 13, 447.
29. Typical Procedure for the Synthesis of Peptidomimetics. Abstract