Facile synthetic route to selectively protected spermidine homologues

Synthetic Communications

Volumn 38, Issue 6, 2008, Pages 905-913

  Andruszkiewicz, Ryszard ^a   Gronek, Ewa ^a   Hałuszczak, Jolanta ^a  

^a GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Hofmann degradation; Michael addition; Polyamines; Protecting groups

Indexed keywords

AMIDE; AMINE; DIAMINE DERIVATIVE; IODOSOBENZENE; SPERMIDINE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CYANOETHYLATION; HOFMANN DEGRADATION; HYDROLYSIS; MICHAEL ADDITION; SYNTHESIS;

EID: 39749183994     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397910701845431     Document Type: Article

References (11)

1. Karigiannis, G.; Papaioannou, D. Structure, biological activity and synthesis of polyamine analogues and conjugates. Eur. J. Org. Chem. 2000, 1841-1863.
2. Kuksa, V.; Buchan, R.; Liu, P. K. T. Synthesis of polyamines, their derivatives, analogues and conjugates. Synthesis 2000, 1189-1207.
3. Chhabra, S. R.; Khan, A. N.; Bycroft, B. W. Solid phase synthesis of polyamines using a Dde-linker: Philanthotoxin-4.3.3 via an On-resin Mitsunobu reaction. Tetrahedron Lett. 2000, 41, 1099-1102.
4. Manov, N.; Bienz, S. A new approach in the solid phase synthesis of polyamine derivatives: Construction of polyamine backbones from center. Tetrahedron 2001, 57, 7893-7898.
5. Kan, T.; Kobayashi, H.; Fukuyama, T. Highly versatile synthesis of polyamines by Ns-strategy on a novel trityl chloride resin. Synlett 2002, 1338-1340.
6. Johnson, D.; Unden, A. Repetitive solid phase synthesis of polyamines. Tetrahedron Lett. 2002, 43, 3125-3128.
7. Czajgucki, Z.; Andruszkiewicz, R.; Kamysz, W. Structure-activity relationship studies on the antimicrobial activity of novel edeine A and D analogues. J. Pept. Sci. 2006, 12, 653-662.
8. Czajgucki, Z.; Zimecki, M.; Andruszkiewicz, R. The immunoregulatory effects of edeine analogues in mice. Cell. Mol. Biol. Lett. 2007, 12, 1490161.
9. 2-benzyloxycarbonyl-(S)-2,4- diaminobutanoic acid. Synth. Commun. 2004, 34, 1049-1056.
10. Krapcho, A. P.; Kuell, C. S. Mono-protected diamines: N-Tert-butoxycarbonyl-α,ω-alkanediamines from α,ω- alkanediamines. Synth. Commun. 1990, 20, 2559-2564.
11. Andruszkiewicz, R.; Radowski, M.; Czajgucki, Z. Efficient synthesis of orthogonally protected spermidine and norspermidine derivatives. Synth. Commun. 2005, 35, 1085-1094.